diff --git a/airflow/tests/test_unit.py b/airflow/tests/test_unit.py
index 033334be280d7..2516311205727 100644
--- a/airflow/tests/test_unit.py
+++ b/airflow/tests/test_unit.py
@@ -31,11 +31,11 @@ def test_service_checks_healthy_exp(aggregator, json_resp, expected_healthy_stat
     check = AirflowCheck('airflow', common.FULL_CONFIG, [instance])
 
     with mock.patch('datadog_checks.airflow.airflow.AirflowCheck._get_version', return_value=None):
-
-        with mock.patch('datadog_checks.base.utils.http.requests') as req:
+        mock_session = mock.MagicMock()
+        with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=mock_session):
             mock_resp = mock.MagicMock(status_code=200)
             mock_resp.json.side_effect = [json_resp]
-            req.get.return_value = mock_resp
+            mock_session.get.return_value = mock_resp
 
             check.check(None)
 
@@ -60,14 +60,14 @@ def test_service_checks_healthy_stable(
     check = AirflowCheck('airflow', common.FULL_CONFIG, [instance])
 
     with mock.patch('datadog_checks.airflow.airflow.AirflowCheck._get_version', return_value='2.6.2'):
-
-        with mock.patch('datadog_checks.base.utils.http.requests') as req:
+        mock_session = mock.MagicMock()
+        with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=mock_session):
             mock_resp = mock.MagicMock(status_code=200)
             mock_resp.json.side_effect = [
                 {'metadatabase': {'status': metadb_status}, 'scheduler': {'status': scheduler_status}},
                 {'status': 'OK'},
             ]
-            req.get.return_value = mock_resp
+            mock_session.get.return_value = mock_resp
 
             check.check(None)
 
@@ -82,7 +82,8 @@ def test_dag_total_tasks(aggregator, task_instance):
     check = AirflowCheck('airflow', common.FULL_CONFIG, [instance])
 
     with mock.patch('datadog_checks.airflow.airflow.AirflowCheck._get_version', return_value='2.6.2'):
-        with mock.patch('datadog_checks.base.utils.http.requests') as req:
+        req = mock.MagicMock()
+        with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
             mock_resp = mock.MagicMock(status_code=200)
             mock_resp.json.side_effect = [
                 {'metadatabase': {'status': 'healthy'}, 'scheduler': {'status': 'healthy'}},
@@ -101,7 +102,8 @@ def test_dag_task_ongoing_duration(aggregator, task_instance):
 
     with mock.patch('datadog_checks.airflow.airflow.AirflowCheck._get_version', return_value='2.6.2'):
 
-        with mock.patch('datadog_checks.base.utils.http.requests') as req:
+        req = mock.MagicMock()
+        with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
             mock_resp = mock.MagicMock(status_code=200)
             mock_resp.json.side_effect = [
                 {'metadatabase': {'status': 'healthy'}, 'scheduler': {'status': 'healthy'}},
@@ -145,7 +147,8 @@ def test_config_collect_ongoing_duration(collect_ongoing_duration, should_call_m
     check = AirflowCheck('airflow', common.FULL_CONFIG, [instance])
 
     with mock.patch('datadog_checks.airflow.airflow.AirflowCheck._get_version', return_value='2.6.2'):
-        with mock.patch('datadog_checks.base.utils.http.requests') as req:
+        req = mock.MagicMock()
+        with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
             mock_resp = mock.MagicMock(status_code=200)
             mock_resp.json.side_effect = [
                 {'metadatabase': {'status': 'healthy'}, 'scheduler': {'status': 'healthy'}},
diff --git a/amazon_msk/tests/conftest.py b/amazon_msk/tests/conftest.py
index 1298134d93e65..ace67250b8fa2 100644
--- a/amazon_msk/tests/conftest.py
+++ b/amazon_msk/tests/conftest.py
@@ -32,6 +32,7 @@ def mock_requests_get(url, *args, **kwargs):
 
 @pytest.fixture
 def mock_data():
+    # Mock requests.get because it is used internally within boto3
     with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
         yield
 
diff --git a/apache/tests/conftest.py b/apache/tests/conftest.py
index 6292ce634df45..63c78ecf14d26 100644
--- a/apache/tests/conftest.py
+++ b/apache/tests/conftest.py
@@ -49,7 +49,8 @@ def check_status_page_ready():
 
 @pytest.fixture
 def mock_hide_server_version():
-    with mock.patch('datadog_checks.base.utils.http.requests') as req:
+    req = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
 
         def mock_requests_get_headers(*args, **kwargs):
             r = requests.get(*args, **kwargs)
diff --git a/arangodb/tests/test_arangodb.py b/arangodb/tests/test_arangodb.py
index 9786150bf5eb0..14ec1ce25b8c1 100644
--- a/arangodb/tests/test_arangodb.py
+++ b/arangodb/tests/test_arangodb.py
@@ -52,11 +52,11 @@ def test_invalid_endpoint(aggregator, instance_invalid_endpoint, dd_run_check):
 def test_check(instance, dd_run_check, aggregator, tag_condition, base_tags):
     check = ArangodbCheck('arangodb', {}, [instance])
 
-    def mock_requests_get(url, *args, **kwargs):
+    def mock_requests_get(session, url, *args, **kwargs):
         fixture = url.rsplit('/', 1)[-1]
         return MockResponse(file_path=os.path.join(os.path.dirname(__file__), 'fixtures', tag_condition, fixture))
 
-    with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+    with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
         dd_run_check(check)
 
     aggregator.assert_service_check(
diff --git a/avi_vantage/tests/conftest.py b/avi_vantage/tests/conftest.py
index 68cbb5fb70668..cb6d79793b997 100644
--- a/avi_vantage/tests/conftest.py
+++ b/avi_vantage/tests/conftest.py
@@ -58,7 +58,8 @@ def _get_metrics(metrics_folder=NO_TENANT_METRICS_FOLDER, endpoint=None):
 
 @pytest.fixture
 def mock_client():
-    with mock.patch('datadog_checks.base.utils.http.requests') as req:
+    req = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
 
         def get(url: AnyStr, *_: Any, **__: Any):
             parsed = urlparse(url)
diff --git a/cert_manager/tests/test_cert_manager.py b/cert_manager/tests/test_cert_manager.py
index b67f638659c27..ee1097015556e 100644
--- a/cert_manager/tests/test_cert_manager.py
+++ b/cert_manager/tests/test_cert_manager.py
@@ -15,7 +15,7 @@
 @pytest.fixture()
 def error_metrics():
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(status_code=502, headers={'Content-Type': "text/plain"}),
     ):
         yield
@@ -34,7 +34,7 @@ def test_check(aggregator, dd_run_check):
     def mock_requests_get(url, *args, **kwargs):
         return MockResponse(file_path=os.path.join(os.path.dirname(__file__), 'fixtures', 'cert_manager.txt'))
 
-    with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+    with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
         dd_run_check(check)
 
     expected_metrics = dict(CERT_METRICS)
diff --git a/cilium/tests/conftest.py b/cilium/tests/conftest.py
index 9df1401331796..2897cc741e53f 100644
--- a/cilium/tests/conftest.py
+++ b/cilium/tests/conftest.py
@@ -203,7 +203,7 @@ def mock_agent_data():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -217,7 +217,7 @@ def mock_operator_data():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/citrix_hypervisor/tests/conftest.py b/citrix_hypervisor/tests/conftest.py
index 01062c83e2f83..9670622329d2e 100644
--- a/citrix_hypervisor/tests/conftest.py
+++ b/citrix_hypervisor/tests/conftest.py
@@ -50,5 +50,5 @@ def mock_requests_get(url, *args, **kwargs):
 
 @pytest.fixture
 def mock_responses():
-    with mock.patch('requests.get', side_effect=mock_requests_get):
+    with mock.patch('requests.Session.get', side_effect=mock_requests_get):
         yield
diff --git a/consul/tests/test_unit.py b/consul/tests/test_unit.py
index 6e93105a5734c..a0588e2a86e77 100644
--- a/consul/tests/test_unit.py
+++ b/consul/tests/test_unit.py
@@ -158,7 +158,7 @@ def test_get_nodes_with_service_critical(aggregator):
 def test_consul_request(aggregator, instance, mocker):
     consul_check = ConsulCheck(common.CHECK_NAME, {}, [consul_mocks.MOCK_CONFIG])
     mocker.patch("datadog_checks.base.utils.serialization.json.loads")
-    with mock.patch("datadog_checks.consul.consul.requests.get") as mock_requests_get:
+    with mock.patch("datadog_checks.consul.consul.requests.Session.get") as mock_requests_get:
         consul_check.consul_request("foo")
         url = "{}/{}".format(instance["url"], "foo")
         aggregator.assert_service_check("consul.can_connect", ConsulCheck.OK, tags=["url:{}".format(url)], count=1)
@@ -549,8 +549,10 @@ def test_config(test_case, extra_config, expected_http_kwargs, mocker):
     check = ConsulCheck(common.CHECK_NAME, {}, instances=[instance])
     mocker.patch("datadog_checks.base.utils.serialization.json.loads")
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
-        r.get.return_value = mock.MagicMock(status_code=200)
+    with mock.patch('datadog_checks.base.utils.http.requests.Session') as session:
+        mock_session = mock.MagicMock()
+        session.return_value = mock_session
+        mock_session.get.return_value = mock.MagicMock(status_code=200)
 
         check.check(None)
 
@@ -564,4 +566,4 @@ def test_config(test_case, extra_config, expected_http_kwargs, mocker):
             'allow_redirects': mock.ANY,
         }
         http_wargs.update(expected_http_kwargs)
-        r.get.assert_called_with('/v1/status/leader', **http_wargs)
+        mock_session.get.assert_called_with('/v1/status/leader', **http_wargs)
diff --git a/couch/tests/test_unit.py b/couch/tests/test_unit.py
index bfa3ba06dadae..7f2ad8678ae2d 100644
--- a/couch/tests/test_unit.py
+++ b/couch/tests/test_unit.py
@@ -30,7 +30,8 @@ def test_config(test_case, extra_config, expected_http_kwargs):
     instance.update(extra_config)
     check = CouchDb(common.CHECK_NAME, {}, instances=[instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200, content='{}')
 
         check.check(instance)
diff --git a/couchbase/tests/test_unit.py b/couchbase/tests/test_unit.py
index ecfb4dec8eb50..a7f0292d2c88a 100644
--- a/couchbase/tests/test_unit.py
+++ b/couchbase/tests/test_unit.py
@@ -72,26 +72,25 @@ def test__get_query_monitoring_data(instance_query):
         ("legacy config", {'user': 'new_foo', 'ssl_verify': False}, {'auth': ('new_foo', 'password'), 'verify': False}),
     ],
 )
-def test_config(test_case, dd_run_check, extra_config, expected_http_kwargs, instance):
+def test_config(test_case, extra_config, expected_http_kwargs, instance):
+    """
+    Test that the legacy and new auth configurations are both supported.
+    """
     instance.update(extra_config)
-    check = Couchbase('couchbase', {}, [instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
-        r.get.return_value = mock.MagicMock(status_code=200)
-
-        dd_run_check(check)
+    check = Couchbase('couchbase', {}, [instance])
 
-        http_wargs = {
-            'auth': mock.ANY,
-            'cert': mock.ANY,
-            'headers': mock.ANY,
-            'proxies': mock.ANY,
-            'timeout': mock.ANY,
-            'verify': mock.ANY,
-            'allow_redirects': mock.ANY,
-        }
-        http_wargs.update(expected_http_kwargs)
-        r.get.assert_called_with('http://localhost:8091/pools/default/tasks', **http_wargs)
+    http_wargs = {
+        'auth': mock.ANY,
+        'cert': mock.ANY,
+        'headers': mock.ANY,
+        'proxies': mock.ANY,
+        'timeout': mock.ANY,
+        'verify': mock.ANY,
+        'allow_redirects': mock.ANY,
+    }
+    http_wargs.update(expected_http_kwargs)
+    assert check.http.options == http_wargs
 
 
 @pytest.mark.parametrize(
@@ -126,7 +125,7 @@ def test_extract_index_tags(instance, test_input, expected_tags):
 
 
 def test_unit(dd_run_check, check, instance, mocker, aggregator):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     dd_run_check(check(instance))
 
@@ -142,7 +141,7 @@ def test_unit(dd_run_check, check, instance, mocker, aggregator):
 
 
 def test_unit_query_metrics(dd_run_check, check, instance_query, mocker, aggregator):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     dd_run_check(check(instance_query))
 
diff --git a/crio/tests/test_crio.py b/crio/tests/test_crio.py
index f6b77953ac2ca..adfd92a32ce34 100644
--- a/crio/tests/test_crio.py
+++ b/crio/tests/test_crio.py
@@ -19,7 +19,7 @@ def mock_data():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/datadog_checks_base/datadog_checks/base/checks/base.py b/datadog_checks_base/datadog_checks/base/checks/base.py
index 6994a39d24524..ab7b45bc378cc 100644
--- a/datadog_checks_base/datadog_checks/base/checks/base.py
+++ b/datadog_checks_base/datadog_checks/base/checks/base.py
@@ -441,7 +441,7 @@ def diagnosis(self) -> Diagnosis:
     def get_tls_context(self, refresh=False, overrides=None):
         # type: (bool, Dict[AnyStr, Any]) -> ssl.SSLContext
         """
-        Creates and cache an SSLContext instance based on user configuration.
+        Creates and cache an TlsContext instance based on user configuration.
         Note that user configuration can be overridden by using `overrides`.
         This should only be applied to older integration that manually set config values.
 
diff --git a/datadog_checks_base/datadog_checks/base/utils/http.py b/datadog_checks_base/datadog_checks/base/utils/http.py
index a21d286f37265..2045c11ade516 100644
--- a/datadog_checks_base/datadog_checks/base/utils/http.py
+++ b/datadog_checks_base/datadog_checks/base/utils/http.py
@@ -27,7 +27,7 @@
 from ..errors import ConfigurationError
 from .common import ensure_bytes, ensure_unicode
 from .headers import get_default_headers, update_headers
-from .network import CertAdapter, create_socket_connection
+from .network import create_socket_connection
 from .time import get_timestamp
 
 # See Performance Optimizations in this package's README.md.
@@ -85,12 +85,14 @@
     'skip_proxy': False,
     'tls_ca_cert': None,
     'tls_cert': None,
+    'tls_ciphers': 'ALL',
     'tls_use_host_header': False,
     'tls_ignore_warning': False,
     'tls_private_key': None,
+    'tls_private_key_password': None,
     'tls_protocols_allowed': DEFAULT_PROTOCOL_VERSIONS,
+    'tls_validate_hostname': True,
     'tls_verify': True,
-    'tls_ciphers': 'ALL',
     'timeout': DEFAULT_TIMEOUT,
     'use_legacy_auth_encoding': True,
     'username': None,
@@ -115,6 +117,100 @@
 UDS_SCHEME = 'unix'
 
 
+def create_ssl_context(config, overrides=None):
+    # https://docs.python.org/3/library/ssl.html#ssl.SSLContext
+    # https://docs.python.org/3/library/ssl.html#ssl.PROTOCOL_TLS_CLIENT
+    context = ssl.SSLContext(protocol=ssl.PROTOCOL_TLS)
+
+    if overrides is not None:
+        config = config.copy()
+        config.update(overrides)
+
+    # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.check_hostname
+    context.check_hostname = config['tls_verify'] and config.get('tls_validate_hostname', True)
+
+    # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.verify_mode
+    context.verify_mode = ssl.CERT_REQUIRED if config['tls_verify'] else ssl.CERT_NONE
+
+    ciphers = config.get('tls_ciphers')
+    if ciphers:
+        if 'ALL' in ciphers:
+            updated_ciphers = "ALL"
+        else:
+            updated_ciphers = ":".join(ciphers)
+
+        context.set_ciphers(updated_ciphers)
+
+    # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.load_verify_locations
+    # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.load_default_certs
+    ca_cert = config['tls_ca_cert']
+    try:
+        if ca_cert:
+            ca_cert = os.path.expanduser(ca_cert)
+            if os.path.isdir(ca_cert):
+                context.load_verify_locations(cafile=None, capath=ca_cert, cadata=None)
+            else:
+                context.load_verify_locations(cafile=ca_cert, capath=None, cadata=None)
+        else:
+            context.load_default_certs(ssl.Purpose.SERVER_AUTH)
+    except FileNotFoundError:
+        LOGGER.warning(
+            'TLS CA certificate file not found: %s. Please check the `tls_ca_cert` configuration option.',
+            ca_cert,
+        )
+
+    # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.load_cert_chain
+    client_cert, client_key = config['tls_cert'], config['tls_private_key']
+    client_key_pass = config['tls_private_key_password']
+    try:
+        if client_key:
+            client_key = os.path.expanduser(client_key)
+        if client_cert:
+            client_cert = os.path.expanduser(client_cert)
+            context.load_cert_chain(client_cert, keyfile=client_key, password=client_key_pass)
+    except FileNotFoundError:
+        LOGGER.warning(
+            'TLS client certificate file not found: %s. ' 'Please check the `tls_cert` configuration option.',
+            client_cert,
+        )
+
+    return context
+
+
+class SSLContextAdapter(requests.adapters.HTTPAdapter):
+    """
+    HTTPS adapter that uses SSL contexts.
+    This ensures consistent TLS configuration across all HTTPS requests.
+    """
+
+    def __init__(self, ssl_context, has_custom_context=False, **kwargs):
+        self.ssl_context = ssl_context
+        # This is used to determine if the adapter was created with a custom context
+        # for the purpose of reverting to the default context when needed.
+        self.has_custom_context = has_custom_context
+        super(SSLContextAdapter, self).__init__()
+
+    def init_poolmanager(self, connections, maxsize, block=False, **pool_kwargs):
+        pool_kwargs['ssl_context'] = self.ssl_context
+        return super(SSLContextAdapter, self).init_poolmanager(connections, maxsize, block=block, **pool_kwargs)
+
+    def cert_verify(self, conn, url, verify, cert):
+        """
+        This method is overridden to ensure that the SSL context
+        is configured on the integration side.
+        """
+        pass
+
+    def build_connection_pool_key_attributes(self, request, verify, cert=None):
+        """
+        This method is overridden according to the requests library's
+        expectations to ensure that the custom SSL context is passed to urllib3.
+        """
+        # See: https://github.com/psf/requests/blob/7341690e842a23cf18ded0abd9229765fa88c4e2/src/requests/adapters.py#L419-L423
+        host_params, _ = super(SSLContextAdapter, self).build_connection_pool_key_attributes(request, verify, cert)
+        return host_params, {"ssl_context": self.ssl_context}
+
+
 class ResponseWrapper(ObjectProxy):
     def __init__(self, response, default_chunk_size):
         super(ResponseWrapper, self).__init__(response)
@@ -152,7 +248,8 @@ class RequestsWrapper(object):
         'auth_token_handler',
         'request_size',
         'tls_protocols_allowed',
-        'tls_ciphers_allowed',
+        'tls_config',
+        'ssl_context',
     )
 
     def __init__(self, instance, init_config, remapper=None, logger=None, session=None):
@@ -254,7 +351,8 @@ def __init__(self, instance, init_config, remapper=None, logger=None, session=No
 
         allow_redirects = is_affirmative(config['allow_redirects'])
 
-        # https://requests.readthedocs.io/en/latest/user/advanced/#ssl-cert-verification
+        # For TLS verification, we now rely on the TLS context wrapper
+        # but still need to set verify for requests compatibility
         verify = True
         if isinstance(config['tls_ca_cert'], str):
             verify = config['tls_ca_cert']
@@ -347,13 +445,9 @@ def __init__(self, instance, init_config, remapper=None, logger=None, session=No
         if config['kerberos_cache']:
             self.request_hooks.append(lambda: handle_kerberos_cache(config['kerberos_cache']))
 
-        ciphers = config.get('tls_ciphers')
-        if ciphers:
-            if 'ALL' in ciphers:
-                updated_ciphers = "ALL"
-            else:
-                updated_ciphers = ":".join(ciphers)
-        self.tls_ciphers_allowed = updated_ciphers
+        # Create TLS context for consistent TLS configuration
+        self.ssl_context = create_ssl_context(config)
+        self.tls_config = {key: value for key, value in config.items() if key.startswith('tls_')}
 
     def get(self, url, **options):
         return self._request('get', url, options)
@@ -406,10 +500,23 @@ def _request(self, method, url, options):
         with ExitStack() as stack:
             for hook in self.request_hooks:
                 stack.enter_context(hook())
+
+            new_context = self._get_new_context(url, new_options)
             if persist:
-                request_method = getattr(self.session, method)
+                session = self.session
+                if new_context is not None:
+                    # If the context has changed, we need to create a new adapter
+                    certadapter = SSLContextAdapter(new_context, has_custom_context=True)
+                    session.mount(url, certadapter)
+                else:
+                    current_adapter = session.get_adapter(url)
+                    if isinstance(current_adapter, SSLContextAdapter) and current_adapter.has_custom_context:
+                        # If we are using a custom context, we need to revert to the original context
+                        certadapter = SSLContextAdapter(self.ssl_context)
+                        session.mount(url, certadapter)
             else:
-                request_method = getattr(requests, method)
+                session = self.create_session(ssl_context=new_context)
+            request_method = getattr(session, method)
 
             if self.auth_token_handler:
                 try:
@@ -424,6 +531,35 @@ def _request(self, method, url, options):
 
             return ResponseWrapper(response, self.request_size)
 
+    def _get_new_context(self, url, new_options):
+        """
+        Creates a new TLS context if the new request options differ from the default ones.
+        """
+        # If `verify` or `cert` options differ from the defaults, a new adapter is created.
+        if new_options.get('verify') == self.options['verify'] and new_options.get('cert') == self.options['cert']:
+            return
+        # If the URL is not HTTPS, no need to update the TLS context.
+        if not url.startswith('https'):
+            return
+
+        request_overrides = {}
+        if new_options.get('verify') != self.options['verify']:
+            if new_options.get('verify') is True:
+                request_overrides["tls_verify"] = True
+            elif new_options.get('verify') is False:
+                request_overrides["tls_verify"] = False
+            elif isinstance(new_options.get('verify'), str):
+                request_overrides["tls_verify"] = True
+                request_overrides["tls_ca_cert"] = new_options.get('verify')
+        if new_options.get('cert') != self.options['cert']:
+            if isinstance(new_options.get('cert'), str):
+                request_overrides["tls_cert"] = new_options.get('cert')
+            elif isinstance(new_options.get('cert'), tuple) and len(new_options.get('cert')) == 2:
+                request_overrides["tls_cert"] = new_options.get('cert')[0]
+                request_overrides["tls_private_key"] = new_options.get('cert')[1]
+
+        return create_ssl_context(self.tls_config, overrides=request_overrides)
+
     def make_request_aia_chasing(self, request_method, method, url, new_options, persist):
         try:
             response = request_method(url, **new_options)
@@ -435,16 +571,15 @@ def make_request_aia_chasing(self, request_method, method, url, new_options, per
             certs = self.fetch_intermediate_certs(hostname, port)
             if not certs:
                 raise e
+            new_context = create_ssl_context(self.tls_config, overrides={'tls_ca_cert': certs})
             # retry the connection via session object
-            certadapter = CertAdapter(certs=certs)
             if not persist:
-                session = requests.Session()
-                for option, value in self.options.items():
-                    setattr(session, option, value)
+                session = self.create_session(new_context)
             else:
                 session = self.session
+                certadapter = SSLContextAdapter(new_context)
+                session.mount(url, certadapter)
             request_method = getattr(session, method)
-            session.mount(url, certadapter)
             response = request_method(url, **new_options)
         return response
 
@@ -471,9 +606,7 @@ def fetch_intermediate_certs(self, hostname, port=443):
 
         with sock:
             try:
-                context = ssl.SSLContext(protocol=ssl.PROTOCOL_TLS)
-                context.verify_mode = ssl.CERT_NONE
-                context.set_ciphers(self.tls_ciphers_allowed)
+                context = create_ssl_context(self.tls_config, overrides={'tls_verify': False})
 
                 with context.wrap_socket(sock, server_hostname=hostname) as secure_sock:
                     der_cert = secure_sock.getpeercert(binary_form=True)
@@ -521,7 +654,7 @@ def load_intermediate_certs(self, der_cert, certs):
 
             # Assume HTTP for now
             try:
-                response = requests.get(uri)  # SKIP_HTTP_VALIDATION
+                response = self.get(uri, verify=False)  # SKIP_HTTP_VALIDATION
             except Exception as e:
                 self.logger.error('Error fetching intermediate certificate from `%s`: %s', uri, e)
                 continue
@@ -532,23 +665,47 @@ def load_intermediate_certs(self, der_cert, certs):
             self.load_intermediate_certs(intermediate_cert, certs)
         return certs
 
-    @property
-    def session(self):
-        if self._session is None:
-            self._session = requests.Session()
+    def create_session(self, ssl_context=None):
+        session = requests.Session()
+        context = self.ssl_context if ssl_context is None else ssl_context
 
-            # Enables HostHeaderSSLAdapter
-            # https://toolbelt.readthedocs.io/en/latest/adapters.html#hostheaderssladapter
-            if self.tls_use_host_header:
-                self._session.mount('https://', _http_utils.HostHeaderSSLAdapter())
-            # Enable Unix Domain Socket (UDS) support.
-            # See: https://github.com/msabramo/requests-unixsocket
-            self._session.mount('{}://'.format(UDS_SCHEME), requests_unixsocket.UnixAdapter())
+        # Enables HostHeaderSSLAdapter if needed
+        # https://toolbelt.readthedocs.io/en/latest/adapters.html#hostheaderssladapter
+        if self.tls_use_host_header:
+            # Create a combined adapter that supports both TLS context and host headers
+            class SSLContextHostHeaderAdapter(SSLContextAdapter, _http_utils.HostHeaderSSLAdapter):
+                def __init__(self, ssl_context, **kwargs):
+                    SSLContextAdapter.__init__(self, ssl_context, **kwargs)
+                    _http_utils.HostHeaderSSLAdapter.__init__(self, **kwargs)
+
+                def init_poolmanager(self, connections, maxsize, block=False, **pool_kwargs):
+                    # Use TLS context from wrapper
+                    pool_kwargs['ssl_context'] = self.ssl_context
+                    return _http_utils.HostHeaderSSLAdapter.init_poolmanager(
+                        self, connections, maxsize, block=block, **pool_kwargs
+                    )
+
+            https_adapter = SSLContextHostHeaderAdapter(context)
+        else:
+            # Use SSLContextHTTPSAdapter for consistent TLS configuration
+            https_adapter = SSLContextAdapter(context)
+
+        session.mount('https://', https_adapter)
 
-            # Attributes can't be passed to the constructor
-            for option, value in self.options.items():
-                setattr(self._session, option, value)
+        # Enable Unix Domain Socket (UDS) support.
+        # See: https://github.com/msabramo/requests-unixsocket
+        session.mount('{}://'.format(UDS_SCHEME), requests_unixsocket.UnixAdapter())
 
+        # Attributes can't be passed to the constructor
+        for option, value in self.options.items():
+            setattr(session, option, value)
+        return session
+
+    @property
+    def session(self):
+        if self._session is None:
+            # Create a new session if it doesn't exist
+            self._session = self.create_session()
         return self._session
 
     def handle_auth_token(self, **request):
diff --git a/datadog_checks_base/datadog_checks/base/utils/network.py b/datadog_checks_base/datadog_checks/base/utils/network.py
index 4c51899f00f3e..c8f135c65a6b3 100644
--- a/datadog_checks_base/datadog_checks/base/utils/network.py
+++ b/datadog_checks_base/datadog_checks/base/utils/network.py
@@ -1,7 +1,4 @@
 import socket
-import ssl
-
-from requests.adapters import HTTPAdapter, PoolManager
 
 
 def create_socket_connection(hostname, port=443, sock_type=socket.SOCK_STREAM, timeout=10):
@@ -34,16 +31,3 @@ def create_socket_connection(hostname, port=443, sock_type=socket.SOCK_STREAM, t
             raise socket.error('Unable to resolve host, check your DNS: {}'.format(message))  # noqa: G
 
         raise
-
-
-class CertAdapter(HTTPAdapter):
-    def __init__(self, **kwargs):
-        self.certs = kwargs['certs']
-        super(CertAdapter, self).__init__()
-
-    def init_poolmanager(self, connections, maxsize, block=False, **pool_kwargs):
-        context = ssl.create_default_context()
-        for cert in self.certs:
-            context.load_verify_locations(cadata=cert)
-        pool_kwargs['ssl_context'] = context
-        self.poolmanager = PoolManager(num_pools=connections, maxsize=maxsize, block=block, strict=True, **pool_kwargs)
diff --git a/datadog_checks_base/datadog_checks/base/utils/tls.py b/datadog_checks_base/datadog_checks/base/utils/tls.py
index 0fb43c028a112..e6fc7643a18dd 100644
--- a/datadog_checks_base/datadog_checks/base/utils/tls.py
+++ b/datadog_checks_base/datadog_checks/base/utils/tls.py
@@ -2,12 +2,11 @@
 # All rights reserved
 # Licensed under a 3-clause BSD style license (see LICENSE)
 import logging
-import os
-import ssl
 from copy import deepcopy
 from typing import TYPE_CHECKING, Any, AnyStr, Dict  # noqa: F401
 
 from ..config import is_affirmative
+from .http import create_ssl_context
 
 if TYPE_CHECKING:
     from ..types import InstanceType  # noqa: F401
@@ -36,7 +35,6 @@ class TlsContextWrapper(object):
     __slots__ = ('logger', 'config', 'tls_context')
 
     def __init__(self, instance, remapper=None, overrides=None):
-        # type: (InstanceType, Dict[AnyStr, Dict[AnyStr, Any]], Dict[AnyStr, Any]) -> None
         default_fields = dict(STANDARD_FIELDS)
 
         # Override existing config options if there exists any overrides
@@ -98,56 +96,8 @@ def __init__(self, instance, remapper=None, overrides=None):
                 del config[unique_name]
 
         self.config = config
-        self.tls_context = self._create_tls_context()
-
-    def _create_tls_context(self):
-        # type: () -> ssl.SSLContext
-
-        # https://docs.python.org/3/library/ssl.html#ssl.SSLContext
-        # https://docs.python.org/3/library/ssl.html#ssl.PROTOCOL_TLS
-        context = ssl.SSLContext(protocol=ssl.PROTOCOL_TLS)
-
-        # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.verify_mode
-        context.verify_mode = ssl.CERT_REQUIRED if self.config['tls_verify'] else ssl.CERT_NONE
-
-        # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.check_hostname
-        if context.verify_mode == ssl.CERT_REQUIRED:
-            context.check_hostname = self.config.get('tls_validate_hostname', True)
-        else:
-            context.check_hostname = False
-
-        ciphers = self.config.get('tls_ciphers')
-        if ciphers:
-            if 'ALL' in ciphers:
-                updated_ciphers = "ALL"
-            else:
-                updated_ciphers = ":".join(ciphers)
-
-            context.set_ciphers(updated_ciphers)
-
-        # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.load_verify_locations
-        # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.load_default_certs
-        ca_cert = self.config['tls_ca_cert']
-        if ca_cert:
-            ca_cert = os.path.expanduser(ca_cert)
-            if os.path.isdir(ca_cert):
-                context.load_verify_locations(cafile=None, capath=ca_cert, cadata=None)
-            else:
-                context.load_verify_locations(cafile=ca_cert, capath=None, cadata=None)
-        else:
-            context.load_default_certs(ssl.Purpose.SERVER_AUTH)
-
-        # https://docs.python.org/3/library/ssl.html#ssl.SSLContext.load_cert_chain
-        client_cert, client_key = self.config['tls_cert'], self.config['tls_private_key']
-        client_key_pass = self.config['tls_private_key_password']
-        if client_key:
-            client_key = os.path.expanduser(client_key)
-        if client_cert:
-            client_cert = os.path.expanduser(client_cert)
-            context.load_cert_chain(client_cert, keyfile=client_key, password=client_key_pass)
-
-        return context
+        self.tls_context = create_ssl_context(self.config)
 
     def refresh_tls_context(self):
         # type: () -> None
-        self.tls_context = self._create_tls_context()
+        self.tls_context = create_ssl_context(self.config)
diff --git a/datadog_checks_base/tests/base/checks/openmetrics/test_legacy/test_openmetrics.py b/datadog_checks_base/tests/base/checks/openmetrics/test_legacy/test_openmetrics.py
index 17341a0fce77b..21b267c970a42 100644
--- a/datadog_checks_base/tests/base/checks/openmetrics/test_legacy/test_openmetrics.py
+++ b/datadog_checks_base/tests/base/checks/openmetrics/test_legacy/test_openmetrics.py
@@ -157,7 +157,7 @@ def test_poll_text_plain(mocked_prometheus_check, mocked_prometheus_scraper_conf
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': text_content_type}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         response = check.poll(mocked_prometheus_scraper_config)
         messages = list(check.parse_metric_family(response, mocked_prometheus_scraper_config))
         messages.sort(key=lambda x: x.name)
@@ -174,7 +174,7 @@ def test_poll_octet_stream(mocked_prometheus_check, mocked_prometheus_scraper_co
     mock_response.status_code = 200
     mock_response.headers = {'Content-Type': 'application/octet-stream'}
 
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         response = check.poll(mocked_prometheus_scraper_config)
         messages = list(check.parse_metric_family(response, mocked_prometheus_scraper_config))
         assert len(messages) == 40
@@ -1695,7 +1695,7 @@ def test_ignore_metrics_multiple_wildcards(
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': text_content_type}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check.process(config)
 
         # Make sure metrics are ignored
@@ -1803,7 +1803,7 @@ def test_metrics_with_ignore_label_values(
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': text_content_type}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check.process(config)
 
         # Make sure metrics are ignored
@@ -1854,7 +1854,7 @@ def test_match_metrics_multiple_wildcards(
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': text_content_type}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check.process(config)
 
         aggregator.assert_metric('prometheus.go_memstats_mcache_inuse_bytes', count=1)
@@ -2304,7 +2304,7 @@ def test_label_joins_gc(aggregator, mocked_prometheus_check, mocked_prometheus_s
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': text_content_type}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check.process(mocked_prometheus_scraper_config)
         assert 'dd-agent-1337' in mocked_prometheus_scraper_config['_label_mapping']['pod']
         assert 'dd-agent-62bgh' not in mocked_prometheus_scraper_config['_label_mapping']['pod']
@@ -2464,7 +2464,7 @@ def test_label_join_state_change(aggregator, mocked_prometheus_check, mocked_pro
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': text_content_type}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check.process(mocked_prometheus_scraper_config)
         assert 15 == len(mocked_prometheus_scraper_config['_label_mapping']['pod'])
         assert mocked_prometheus_scraper_config['_label_mapping']['pod']['dd-agent-62bgh']['phase'] == 'Test'
@@ -2582,7 +2582,7 @@ def mock_filter_get():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: text_data.split("\n"),
@@ -2672,7 +2672,7 @@ def test_ssl_verify_not_raise_warning(caplog, mocked_openmetrics_check_factory,
     check = mocked_openmetrics_check_factory(instance)
     scraper_config = check.get_scraper_config(instance)
 
-    with caplog.at_level(logging.DEBUG), mock.patch('requests.get', return_value=MockResponse('httpbin.org')):
+    with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get', return_value=MockResponse('httpbin.org')):
         resp = check.send_request('https://httpbin.org/get', scraper_config)
 
     assert "httpbin.org" in resp.content.decode('utf-8')
@@ -2696,7 +2696,7 @@ def test_send_request_with_dynamic_prometheus_url(caplog, mocked_openmetrics_che
     # `prometheus_url` changed just before calling `send_request`
     scraper_config['prometheus_url'] = 'https://www.example.com/foo/bar'
 
-    with caplog.at_level(logging.DEBUG), mock.patch('requests.get', return_value=MockResponse('httpbin.org')):
+    with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get', return_value=MockResponse('httpbin.org')):
         resp = check.send_request('https://httpbin.org/get', scraper_config)
 
     assert "httpbin.org" in resp.content.decode('utf-8')
diff --git a/datadog_checks_base/tests/base/checks/prometheus/test_prometheus.py b/datadog_checks_base/tests/base/checks/prometheus/test_prometheus.py
index a3a997aaf1b75..0625a62989f38 100644
--- a/datadog_checks_base/tests/base/checks/prometheus/test_prometheus.py
+++ b/datadog_checks_base/tests/base/checks/prometheus/test_prometheus.py
@@ -5,6 +5,7 @@
 # Licensed under Simplified BSD License (see LICENSE)
 import logging
 import os
+import ssl
 from collections import OrderedDict
 
 import mock
@@ -334,7 +335,7 @@ def test_poll_protobuf(mocked_prometheus_check, bin_data):
     """Tests poll using the protobuf format"""
     check = mocked_prometheus_check
     mock_response = mock.MagicMock(status_code=200, content=bin_data, headers={'Content-Type': protobuf_content_type})
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         response = check.poll("http://fake.endpoint:10055/metrics")
         messages = list(check.parse_metric_family(response))
         assert len(messages) == 61
@@ -347,7 +348,7 @@ def test_poll_text_plain(mocked_prometheus_check, text_data):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         response = check.poll("http://fake.endpoint:10055/metrics")
         messages = list(check.parse_metric_family(response))
         messages.sort(key=lambda x: x.name)
@@ -1284,7 +1285,7 @@ def test_label_joins(sorted_tags_check):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check = sorted_tags_check
         check.NAMESPACE = 'ksm'
         check.label_joins = {
@@ -1634,7 +1635,7 @@ def test_label_joins_gc(sorted_tags_check):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check = sorted_tags_check
         check.NAMESPACE = 'ksm'
         check.label_joins = {'kube_pod_info': {'label_to_match': 'pod', 'labels_to_get': ['node', 'pod_ip']}}
@@ -1684,7 +1685,7 @@ def test_label_joins_gc(sorted_tags_check):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check.process("http://fake.endpoint:10055/metrics")
         assert 'dd-agent-1337' in check._label_mapping['pod']
         assert 'dd-agent-62bgh' not in check._label_mapping['pod']
@@ -1700,7 +1701,7 @@ def test_label_joins_missconfigured(sorted_tags_check):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check = sorted_tags_check
         check.NAMESPACE = 'ksm'
         check.label_joins = {'kube_pod_info': {'label_to_match': 'pod', 'labels_to_get': ['node', 'not_existing']}}
@@ -1753,7 +1754,7 @@ def test_label_join_not_existing(sorted_tags_check):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check = sorted_tags_check
         check.NAMESPACE = 'ksm'
         check.label_joins = {'kube_pod_info': {'label_to_match': 'not_existing', 'labels_to_get': ['node', 'pod_ip']}}
@@ -1792,7 +1793,7 @@ def test_label_join_metric_not_existing(sorted_tags_check):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check = sorted_tags_check
         check.NAMESPACE = 'ksm'
         check.label_joins = {'not_existing': {'label_to_match': 'pod', 'labels_to_get': ['node', 'pod_ip']}}
@@ -1831,7 +1832,7 @@ def test_label_join_with_hostname(sorted_tags_check):
     mock_response = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
     )
-    with mock.patch('requests.get', return_value=mock_response, __name__="get"):
+    with mock.patch('requests.Session.get', return_value=mock_response, __name__="get"):
         check = sorted_tags_check
         check.NAMESPACE = 'ksm'
         check.label_joins = {'kube_pod_info': {'label_to_match': 'pod', 'labels_to_get': ['node']}}
@@ -1883,7 +1884,7 @@ def mock_get():
     with open(f_name, 'r') as f:
         text_data = f.read()
     mock_get = mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -1966,7 +1967,7 @@ def test_ssl_verify_not_raise_warning(caplog, mocked_prometheus_check, text_data
 
     check = mocked_prometheus_check
 
-    with caplog.at_level(logging.DEBUG), mock.patch('requests.get', return_value=MockResponse('httpbin.org')):
+    with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get', return_value=MockResponse('httpbin.org')):
         resp = check.poll('https://httpbin.org/get')
 
     assert 'httpbin.org' in resp.content.decode('utf-8')
@@ -1982,7 +1983,7 @@ def test_ssl_verify_not_raise_warning_cert_false(caplog, mocked_prometheus_check
     check = mocked_prometheus_check
     check.ssl_ca_cert = False
 
-    with caplog.at_level(logging.DEBUG), mock.patch('requests.get', return_value=MockResponse('httpbin.org')):
+    with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get', return_value=MockResponse('httpbin.org')):
         resp = check.poll('https://httpbin.org/get')
 
     assert 'httpbin.org' in resp.content.decode('utf-8')
@@ -2018,29 +2019,32 @@ def test_requests_wrapper_config():
         ]
     )
 
-    with mock.patch("requests.get") as get:
-        check.poll(instance_http['prometheus_endpoint'], instance=instance_http)
-        get.assert_called_with(
-            instance_http['prometheus_endpoint'],
-            stream=False,
-            headers=expected_headers,
-            auth=requests.auth.HTTPDigestAuth('data', 'dog'),
-            cert='/path/to/cert',
-            timeout=(42.0, 42.0),
-            proxies=None,
-            verify=True,
-            allow_redirects=True,
-        )
-
-        check.poll(instance_http['prometheus_endpoint'])
-        get.assert_called_with(
-            instance_http['prometheus_endpoint'],
-            stream=False,
-            headers=expected_headers,
-            auth=requests.auth.HTTPDigestAuth('data', 'dog'),
-            cert='/path/to/cert',
-            timeout=(42.0, 42.0),
-            proxies=None,
-            verify=True,
-            allow_redirects=True,
-        )
+    with mock.patch("requests.Session.get") as get:
+        with mock.patch.object(ssl.SSLContext, 'load_cert_chain') as mock_load_cert_chain:
+            mock_load_cert_chain.return_value = None
+
+            check.poll(instance_http['prometheus_endpoint'], instance=instance_http)
+            get.assert_called_with(
+                instance_http['prometheus_endpoint'],
+                stream=False,
+                headers=expected_headers,
+                auth=requests.auth.HTTPDigestAuth('data', 'dog'),
+                cert='/path/to/cert',
+                timeout=(42.0, 42.0),
+                proxies=None,
+                verify=True,
+                allow_redirects=True,
+            )
+
+            check.poll(instance_http['prometheus_endpoint'])
+            get.assert_called_with(
+                instance_http['prometheus_endpoint'],
+                stream=False,
+                headers=expected_headers,
+                auth=requests.auth.HTTPDigestAuth('data', 'dog'),
+                cert='/path/to/cert',
+                timeout=(42.0, 42.0),
+                proxies=None,
+                verify=True,
+                allow_redirects=True,
+            )
diff --git a/datadog_checks_base/tests/base/utils/http/test_api.py b/datadog_checks_base/tests/base/utils/http/test_api.py
index 3440c300147d2..6986ae297d477 100644
--- a/datadog_checks_base/tests/base/utils/http/test_api.py
+++ b/datadog_checks_base/tests/base/utils/http/test_api.py
@@ -13,9 +13,9 @@
 def test_get():
     http = RequestsWrapper({}, {})
 
-    with mock.patch('requests.get'):
+    with mock.patch('requests.Session.get'):
         http.get('https://www.google.com')
-        requests.get.assert_called_once_with('https://www.google.com', **http.options)
+        requests.Session.get.assert_called_once_with('https://www.google.com', **http.options)
 
 
 def test_get_session():
@@ -31,9 +31,9 @@ def test_get_option_override():
     options = http.options.copy()
     options['auth'] = ('user', 'pass')
 
-    with mock.patch('requests.get'):
+    with mock.patch('requests.Session.get'):
         http.get('https://www.google.com', auth=options['auth'])
-        requests.get.assert_called_once_with('https://www.google.com', **options)
+        requests.Session.get.assert_called_once_with('https://www.google.com', **options)
 
 
 def test_get_session_option_override():
@@ -49,9 +49,9 @@ def test_get_session_option_override():
 def test_post():
     http = RequestsWrapper({}, {})
 
-    with mock.patch('requests.post'):
+    with mock.patch('requests.Session.post'):
         http.post('https://www.google.com')
-        requests.post.assert_called_once_with('https://www.google.com', **http.options)
+        requests.Session.post.assert_called_once_with('https://www.google.com', **http.options)
 
 
 def test_post_session():
@@ -67,9 +67,9 @@ def test_post_option_override():
     options = http.options.copy()
     options['auth'] = ('user', 'pass')
 
-    with mock.patch('requests.post'):
+    with mock.patch('requests.Session.post'):
         http.post('https://www.google.com', auth=options['auth'])
-        requests.post.assert_called_once_with('https://www.google.com', **options)
+        requests.Session.post.assert_called_once_with('https://www.google.com', **options)
 
 
 def test_post_session_option_override():
@@ -85,9 +85,9 @@ def test_post_session_option_override():
 def test_head():
     http = RequestsWrapper({}, {})
 
-    with mock.patch('requests.head'):
+    with mock.patch('requests.Session.head'):
         http.head('https://www.google.com')
-        requests.head.assert_called_once_with('https://www.google.com', **http.options)
+        requests.Session.head.assert_called_once_with('https://www.google.com', **http.options)
 
 
 def test_head_session():
@@ -103,9 +103,9 @@ def test_head_option_override():
     options = http.options.copy()
     options['auth'] = ('user', 'pass')
 
-    with mock.patch('requests.head'):
+    with mock.patch('requests.Session.head'):
         http.head('https://www.google.com', auth=options['auth'])
-        requests.head.assert_called_once_with('https://www.google.com', **options)
+        requests.Session.head.assert_called_once_with('https://www.google.com', **options)
 
 
 def test_head_session_option_override():
@@ -121,9 +121,9 @@ def test_head_session_option_override():
 def test_put():
     http = RequestsWrapper({}, {})
 
-    with mock.patch('requests.put'):
+    with mock.patch('requests.Session.put'):
         http.put('https://www.google.com')
-        requests.put.assert_called_once_with('https://www.google.com', **http.options)
+        requests.Session.put.assert_called_once_with('https://www.google.com', **http.options)
 
 
 def test_put_session():
@@ -139,9 +139,9 @@ def test_put_option_override():
     options = http.options.copy()
     options['auth'] = ('user', 'pass')
 
-    with mock.patch('requests.put'):
+    with mock.patch('requests.Session.put'):
         http.put('https://www.google.com', auth=options['auth'])
-        requests.put.assert_called_once_with('https://www.google.com', **options)
+        requests.Session.put.assert_called_once_with('https://www.google.com', **options)
 
 
 def test_put_session_option_override():
@@ -157,9 +157,9 @@ def test_put_session_option_override():
 def test_patch():
     http = RequestsWrapper({}, {})
 
-    with mock.patch('requests.patch'):
+    with mock.patch('requests.Session.patch'):
         http.patch('https://www.google.com')
-        requests.patch.assert_called_once_with('https://www.google.com', **http.options)
+        requests.Session.patch.assert_called_once_with('https://www.google.com', **http.options)
 
 
 def test_patch_session():
@@ -175,9 +175,9 @@ def test_patch_option_override():
     options = http.options.copy()
     options['auth'] = ('user', 'pass')
 
-    with mock.patch('requests.patch'):
+    with mock.patch('requests.Session.patch'):
         http.patch('https://www.google.com', auth=options['auth'])
-        requests.patch.assert_called_once_with('https://www.google.com', **options)
+        requests.Session.patch.assert_called_once_with('https://www.google.com', **options)
 
 
 def test_patch_session_option_override():
@@ -193,9 +193,9 @@ def test_patch_session_option_override():
 def test_delete():
     http = RequestsWrapper({}, {})
 
-    with mock.patch('requests.delete'):
+    with mock.patch('requests.Session.delete'):
         http.delete('https://www.google.com')
-        requests.delete.assert_called_once_with('https://www.google.com', **http.options)
+        requests.Session.delete.assert_called_once_with('https://www.google.com', **http.options)
 
 
 def test_delete_session():
@@ -211,9 +211,9 @@ def test_delete_option_override():
     options = http.options.copy()
     options['auth'] = ('user', 'pass')
 
-    with mock.patch('requests.delete'):
+    with mock.patch('requests.Session.delete'):
         http.delete('https://www.google.com', auth=options['auth'])
-        requests.delete.assert_called_once_with('https://www.google.com', **options)
+        requests.Session.delete.assert_called_once_with('https://www.google.com', **options)
 
 
 def test_delete_session_option_override():
@@ -229,9 +229,9 @@ def test_delete_session_option_override():
 def test_options():
     http = RequestsWrapper({}, {})
 
-    with mock.patch('requests.options'):
+    with mock.patch('requests.Session.options'):
         http.options_method('https://www.google.com')
-        requests.options.assert_called_once_with('https://www.google.com', **http.options)
+        requests.Session.options.assert_called_once_with('https://www.google.com', **http.options)
 
 
 def test_options_session():
@@ -247,9 +247,9 @@ def test_options_option_override():
     options = http.options.copy()
     options['auth'] = ('user', 'pass')
 
-    with mock.patch('requests.options'):
+    with mock.patch('requests.Session.options'):
         http.options_method('https://www.google.com', auth=options['auth'])
-        requests.options.assert_called_once_with('https://www.google.com', **options)
+        requests.Session.options.assert_called_once_with('https://www.google.com', **options)
 
 
 def test_options_session_option_override():
diff --git a/datadog_checks_base/tests/base/utils/http/test_authtoken.py b/datadog_checks_base/tests/base/utils/http/test_authtoken.py
index 6b6913c80093a..c4edab004339b 100644
--- a/datadog_checks_base/tests/base/utils/http/test_authtoken.py
+++ b/datadog_checks_base/tests/base/utils/http/test_authtoken.py
@@ -399,7 +399,7 @@ def test_pattern_no_match(self):
             init_config = {}
             http = RequestsWrapper(instance, init_config)
 
-            with mock.patch('requests.get'):
+            with mock.patch('requests.Session.get'):
                 write_file(token_file, '\nsecret\nsecret\n')
 
                 with pytest.raises(
@@ -424,7 +424,7 @@ def test_pattern_match(self):
 
             expected_headers = {'Authorization': 'Bearer bar'}
             expected_headers.update(DEFAULT_OPTIONS['headers'])
-            with mock.patch('requests.get') as get:
+            with mock.patch('requests.Session.get') as get:
                 write_file(token_file, '\nfoobar\nfoobaz\n')
                 http.get('https://www.google.com')
 
@@ -463,7 +463,7 @@ def __init__(self, *args, **kwargs):
             def fetch_token(self, *args, **kwargs):
                 return {'error': 'unauthorized_client'}
 
-        with mock.patch('requests.get'), mock.patch('oauthlib.oauth2.BackendApplicationClient'), mock.patch(
+        with mock.patch('requests.Session.get'), mock.patch('oauthlib.oauth2.BackendApplicationClient'), mock.patch(
             'requests_oauthlib.OAuth2Session', side_effect=MockOAuth2Session
         ):
             with pytest.raises(Exception, match='OAuth2 client credentials grant error: unauthorized_client'):
@@ -503,9 +503,11 @@ def __init__(self, *args, **kwargs):
             def fetch_token(self, *args, **kwargs):
                 return token_response
 
-        with mock.patch('requests.get') as get, mock.patch('oauthlib.oauth2.BackendApplicationClient'), mock.patch(
-            'requests_oauthlib.OAuth2Session', side_effect=MockOAuth2Session
-        ), mock.patch('datadog_checks.base.utils.http.get_timestamp', return_value=0):
+        with mock.patch('requests.Session.get') as get, mock.patch(
+            'oauthlib.oauth2.BackendApplicationClient'
+        ), mock.patch('requests_oauthlib.OAuth2Session', side_effect=MockOAuth2Session), mock.patch(
+            'datadog_checks.base.utils.http.get_timestamp', return_value=0
+        ):
             http.get('https://www.google.com')
 
             get.assert_called_with(
@@ -550,9 +552,9 @@ def fetch_token(self, *args, **kwargs):
                 assert kwargs['audience'] == 'http://example.com'
                 return {'access_token': 'foo', 'expires_in': 9000}
 
-        with mock.patch('requests.get') as get, mock.patch('oauthlib.oauth2.BackendApplicationClient'), mock.patch(
-            'requests_oauthlib.OAuth2Session', side_effect=MockOAuth2Session
-        ):
+        with mock.patch('requests.Session.get') as get, mock.patch(
+            'oauthlib.oauth2.BackendApplicationClient'
+        ), mock.patch('requests_oauthlib.OAuth2Session', side_effect=MockOAuth2Session):
             http.get('https://www.google.com')
 
             get.assert_called_with(
@@ -610,7 +612,9 @@ def auth(*args, **kwargs):
             return MockResponse(status_code=404)
 
         http = RequestsWrapper(instance, init_config)
-        with mock.patch('requests.post', side_effect=login), mock.patch('requests.get', side_effect=auth):
+        with mock.patch('requests.Session.post', side_effect=login), mock.patch(
+            'requests.Session.get', side_effect=auth
+        ):
             http.get('https://leader.mesos/service/some-service')
 
 
@@ -629,7 +633,7 @@ def test_default_placeholder_same_as_value(self):
 
             expected_headers = {'X-Vault-Token': 'foobar'}
             expected_headers.update(DEFAULT_OPTIONS['headers'])
-            with mock.patch('requests.get') as get:
+            with mock.patch('requests.Session.get') as get:
                 write_file(token_file, '\nfoobar\n')
                 http.get('https://www.google.com')
 
@@ -662,7 +666,7 @@ def test_read_before_first_request(self):
 
             expected_headers = {'Authorization': 'Bearer secret1'}
             expected_headers.update(DEFAULT_OPTIONS['headers'])
-            with mock.patch('requests.get') as get:
+            with mock.patch('requests.Session.get') as get:
                 write_file(token_file, '\nsecret1\n')
                 http.get('https://www.google.com')
 
@@ -708,7 +712,7 @@ def test_refresh_after_connection_error(self):
             init_config = {}
             http = RequestsWrapper(instance, init_config)
 
-            with mock.patch('requests.get'):
+            with mock.patch('requests.Session.get'):
                 write_file(token_file, '\nsecret1\n')
                 http.get('https://www.google.com')
 
@@ -723,7 +727,7 @@ def raise_error_once(*args, **kwargs):
 
             expected_headers = {'Authorization': 'Bearer secret2'}
             expected_headers.update(DEFAULT_OPTIONS['headers'])
-            with mock.patch('requests.get', side_effect=raise_error_once) as get:
+            with mock.patch('requests.Session.get', side_effect=raise_error_once) as get:
                 write_file(token_file, '\nsecret2\n')
 
                 http.get('https://www.google.com')
@@ -753,7 +757,7 @@ def test_refresh_after_bad_status_code(self):
             init_config = {}
             http = RequestsWrapper(instance, init_config)
 
-            with mock.patch('requests.get'):
+            with mock.patch('requests.Session.get'):
                 write_file(token_file, '\nsecret1\n')
                 http.get('https://www.google.com')
 
@@ -762,7 +766,7 @@ def error():
 
             expected_headers = {'Authorization': 'Bearer secret2'}
             expected_headers.update(DEFAULT_OPTIONS['headers'])
-            with mock.patch('requests.get', return_value=mock.MagicMock(raise_for_status=error)) as get:
+            with mock.patch('requests.Session.get', return_value=mock.MagicMock(raise_for_status=error)) as get:
                 write_file(token_file, '\nsecret2\n')
                 http.get('https://www.google.com')
 
diff --git a/datadog_checks_base/tests/base/utils/http/test_config.py b/datadog_checks_base/tests/base/utils/http/test_config.py
index 5080f231d4fe1..8263c48b1a90e 100644
--- a/datadog_checks_base/tests/base/utils/http/test_config.py
+++ b/datadog_checks_base/tests/base/utils/http/test_config.py
@@ -1,6 +1,10 @@
 # (C) Datadog, Inc. 2022-present
 # All rights reserved
 # Licensed under a 3-clause BSD style license (see LICENSE)
+import ssl
+
+import mock
+
 from datadog_checks.base.utils.http import STANDARD_FIELDS, RequestsWrapper
 
 
@@ -72,16 +76,23 @@ def test_config_verify(self):
     def test_config_ca_cert(self):
         instance = {'tls_ca_cert': 'ca_cert'}
         init_config = {}
-        http = RequestsWrapper(instance, init_config)
 
-        assert http.options['verify'] == 'ca_cert'
+        with mock.patch.object(ssl.SSLContext, 'load_verify_locations') as mock_load_verify_locations:
+            RequestsWrapper(instance, init_config)
+
+            assert mock_load_verify_locations.call_count == 1
+            assert mock_load_verify_locations.call_args[1]['cafile'] == 'ca_cert'
 
     def test_config_verify_and_ca_cert(self):
         instance = {'tls_verify': True, 'tls_ca_cert': 'ca_cert'}
         init_config = {}
-        http = RequestsWrapper(instance, init_config)
 
-        assert http.options['verify'] == 'ca_cert'
+        with mock.patch.object(ssl.SSLContext, 'load_verify_locations') as mock_load_verify_locations:
+            http = RequestsWrapper(instance, init_config)
+
+            assert http.options['verify'] == 'ca_cert'
+            assert mock_load_verify_locations.call_count == 1
+            assert mock_load_verify_locations.call_args[1]['cafile'] == 'ca_cert'
 
 
 class TestRemapper:
diff --git a/datadog_checks_base/tests/base/utils/http/test_headers.py b/datadog_checks_base/tests/base/utils/http/test_headers.py
index 030561e9993ec..ab42172973153 100644
--- a/datadog_checks_base/tests/base/utils/http/test_headers.py
+++ b/datadog_checks_base/tests/base/utils/http/test_headers.py
@@ -77,7 +77,7 @@ def test_extra_headers_on_http_method_call():
     complete_headers.update({'answer': '42'})
 
     extra_headers = {"foo": "bar"}
-    with mock.patch("requests.get") as get:
+    with mock.patch("requests.Session.get") as get:
         http.get("http://example.com/hello", extra_headers=extra_headers)
 
         expected_options = dict(complete_headers)
diff --git a/datadog_checks_base/tests/base/utils/http/test_http.py b/datadog_checks_base/tests/base/utils/http/test_http.py
index 23e426d5cb26d..8b7270eb96c52 100644
--- a/datadog_checks_base/tests/base/utils/http/test_http.py
+++ b/datadog_checks_base/tests/base/utils/http/test_http.py
@@ -50,13 +50,12 @@ class TestTLSCiphers:
     )
     def test_cipher_construction(self, instance, expected_ciphers):
         init_config = {}
-        http = RequestsWrapper(instance, init_config)
-        mock_socket = mock.MagicMock()
 
-        with mock.patch.object(ssl.SSLContext, 'set_ciphers') as mock_set_ciphers, mock.patch(
-            'datadog_checks.base.utils.http.create_socket_connection', return_value=mock_socket
-        ):
-            http.fetch_intermediate_certs('https://www.google.com')
+        # Mock SSL context creation before RequestsWrapper initialization
+        with mock.patch.object(ssl.SSLContext, 'set_ciphers') as mock_set_ciphers:
+            RequestsWrapper(instance, init_config)
+
+            # Verify that set_ciphers was called with the expected ciphers during TLS context creation
             mock_set_ciphers.assert_called_once_with(expected_ciphers)
 
 
@@ -176,7 +175,7 @@ class TestLogger:
     def test_default(self, caplog):
         check = AgentCheck('test', {}, [{}])
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             check.http.get('https://www.google.com')
 
         expected_message = 'Sending GET request to https://www.google.com'
@@ -190,7 +189,7 @@ def test_instance(self, caplog):
 
         assert check.http.logger is check.log
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             check.http.get('https://www.google.com')
 
         expected_message = 'Sending GET request to https://www.google.com'
@@ -207,7 +206,7 @@ def test_init_config(self, caplog):
 
         assert check.http.logger is check.log
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             check.http.get('https://www.google.com')
 
         expected_message = 'Sending GET request to https://www.google.com'
@@ -222,7 +221,7 @@ def test_instance_override(self, caplog):
         init_config = {'log_requests': True}
         check = AgentCheck('test', init_config, [instance])
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             check.http.get('https://www.google.com')
 
         expected_message = 'Sending GET request to https://www.google.com'
diff --git a/datadog_checks_base/tests/base/utils/http/test_kerberos_unit.py b/datadog_checks_base/tests/base/utils/http/test_kerberos_unit.py
index 2e6ba622bd541..fd4a51a07b0e6 100644
--- a/datadog_checks_base/tests/base/utils/http/test_kerberos_unit.py
+++ b/datadog_checks_base/tests/base/utils/http/test_kerberos_unit.py
@@ -114,7 +114,8 @@ def test_config_kerberos_keytab_file():
     assert os.environ.get('KRB5_CLIENT_KTNAME') is None
 
     with mock.patch(
-        'requests.get', side_effect=lambda *args, **kwargs: MockResponse(os.environ.get('KRB5_CLIENT_KTNAME', ''))
+        'requests.Session.get',
+        side_effect=lambda *args, **kwargs: MockResponse(os.environ.get('KRB5_CLIENT_KTNAME', '')),
     ):
         response = http.get('https://www.google.com')
         assert response.text == '/test/file'
@@ -130,7 +131,9 @@ def test_config_kerberos_cache():
 
     assert os.environ.get('KRB5CCNAME') is None
 
-    with mock.patch('requests.get', side_effect=lambda *args, **kwargs: MockResponse(os.environ.get('KRB5CCNAME', ''))):
+    with mock.patch(
+        'requests.Session.get', side_effect=lambda *args, **kwargs: MockResponse(os.environ.get('KRB5CCNAME', ''))
+    ):
         response = http.get('https://www.google.com')
         assert response.text == '/test/file'
 
@@ -145,7 +148,7 @@ def test_config_kerberos_cache_restores_rollback():
 
     with EnvVars({'KRB5CCNAME': 'old'}):
         with mock.patch(
-            'requests.get', side_effect=lambda *args, **kwargs: MockResponse(os.environ.get('KRB5CCNAME', ''))
+            'requests.Session.get', side_effect=lambda *args, **kwargs: MockResponse(os.environ.get('KRB5CCNAME', ''))
         ):
             response = http.get('https://www.google.com')
             assert response.text == '/test/file'
@@ -163,7 +166,7 @@ def test_config_kerberos_keytab_file_rollback():
         assert os.environ.get('KRB5_CLIENT_KTNAME') == 'old'
 
         with mock.patch(
-            'requests.get',
+            'requests.Session.get',
             side_effect=lambda *args, **kwargs: MockResponse(os.environ.get('KRB5_CLIENT_KTNAME', '')),
         ):
             response = http.get('https://www.google.com')
diff --git a/datadog_checks_base/tests/base/utils/http/test_proxy.py b/datadog_checks_base/tests/base/utils/http/test_proxy.py
index ff8251b82b11a..c9b6898ce7113 100644
--- a/datadog_checks_base/tests/base/utils/http/test_proxy.py
+++ b/datadog_checks_base/tests/base/utils/http/test_proxy.py
@@ -198,23 +198,24 @@ def test_no_proxy_uris_coverage():
         ),
     ],
 )
-@mock.patch('datadog_checks.base.utils.http.requests')
-def test_proxy_passes_right_params_to_requests(requests, proxy, expected_proxy, url):
+def test_proxy_passes_right_params_to_requests(proxy, expected_proxy, url):
     instance = {'proxy': proxy}
     init_config = {}
 
     http = RequestsWrapper(instance, init_config)
-    http.get(url)
 
-    call_args = {
-        'auth': None,
-        'cert': None,
-        'headers': OrderedDict(
-            [('User-Agent', 'Datadog Agent/0.0.0'), ('Accept', '*/*'), ('Accept-Encoding', 'gzip, deflate')]
-        ),
-        'proxies': expected_proxy,
-        'timeout': (10.0, 10.0),
-        'verify': True,
-        'allow_redirects': True,
-    }
-    requests.get.assert_called_with(url, **call_args)
+    with mock.patch('requests.Session.get') as mock_get:
+        http.get(url)
+
+        call_args = {
+            'auth': None,
+            'cert': None,
+            'headers': OrderedDict(
+                [('User-Agent', 'Datadog Agent/0.0.0'), ('Accept', '*/*'), ('Accept-Encoding', 'gzip, deflate')]
+            ),
+            'proxies': expected_proxy,
+            'timeout': (10.0, 10.0),
+            'verify': True,
+            'allow_redirects': True,
+        }
+        mock_get.assert_called_with(url, **call_args)
diff --git a/datadog_checks_base/tests/base/utils/http/test_tls_and_certs.py b/datadog_checks_base/tests/base/utils/http/test_tls_and_certs.py
index 3301a6a8f39c8..481ea658e0159 100644
--- a/datadog_checks_base/tests/base/utils/http/test_tls_and_certs.py
+++ b/datadog_checks_base/tests/base/utils/http/test_tls_and_certs.py
@@ -2,15 +2,21 @@
 # All rights reserved
 # Licensed under a 3-clause BSD style license (see LICENSE)
 import logging
+import ssl
 
 import mock
 import pytest
 from requests.exceptions import SSLError
 
-from datadog_checks.base.utils.http import RequestsWrapper
+from datadog_checks.base.utils.http import RequestsWrapper, SSLContextAdapter
 
 pytestmark = [pytest.mark.unit]
 
+IANA_TO_OPENSSL_NAME = {
+    'TLS_RSA_WITH_AES_256_GCM_SHA384': 'AES256-GCM-SHA384',
+    'TLS_RSA_WITH_AES_128_GCM_SHA256': 'AES128-GCM-SHA256',
+}
+
 
 class TestCert:
     def test_config_default(self):
@@ -23,16 +29,23 @@ def test_config_default(self):
     def test_config_cert(self):
         instance = {'tls_cert': 'cert'}
         init_config = {}
-        http = RequestsWrapper(instance, init_config)
 
-        assert http.options['cert'] == 'cert'
+        with mock.patch.object(ssl.SSLContext, 'load_cert_chain') as mock_load_cert_chain:
+            RequestsWrapper(instance, init_config)
+
+            assert mock_load_cert_chain.call_count == 1
+            assert mock_load_cert_chain.call_args[0][0] == 'cert'
 
     def test_config_cert_and_private_key(self):
         instance = {'tls_cert': 'cert', 'tls_private_key': 'key'}
         init_config = {}
-        http = RequestsWrapper(instance, init_config)
 
-        assert http.options['cert'] == ('cert', 'key')
+        with mock.patch.object(ssl.SSLContext, 'load_cert_chain') as mock_load_cert_chain:
+            RequestsWrapper(instance, init_config)
+
+            assert mock_load_cert_chain.call_count == 1
+            assert mock_load_cert_chain.call_args[0][0] == 'cert'
+            assert mock_load_cert_chain.call_args[1]["keyfile"] == 'key'
 
 
 class TestIgnoreTLSWarning:
@@ -71,7 +84,7 @@ def test_default_no_ignore(self, caplog):
         init_config = {}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -86,7 +99,7 @@ def test_default_no_ignore_http(self, caplog):
         init_config = {}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('http://www.google.com', verify=False)
 
         assert sum(1 for _, level, _ in caplog.record_tuples if level == logging.WARNING) == 0
@@ -96,7 +109,7 @@ def test_ignore(self, caplog):
         init_config = {}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -108,7 +121,7 @@ def test_default_no_ignore_session(self, caplog):
         init_config = {}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -123,7 +136,7 @@ def test_ignore_session(self, caplog):
         init_config = {}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -135,7 +148,7 @@ def test_init_ignore(self, caplog):
         init_config = {'tls_ignore_warning': True}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -147,7 +160,7 @@ def test_default_init_no_ignore(self, caplog):
         init_config = {'tls_ignore_warning': False}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -162,7 +175,7 @@ def test_instance_ignore(self, caplog):
         init_config = {'tls_ignore_warning': False}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -174,7 +187,7 @@ def test_instance_no_ignore(self, caplog):
         init_config = {'tls_ignore_warning': True}
         http = RequestsWrapper(instance, init_config)
 
-        with caplog.at_level(logging.DEBUG), mock.patch('requests.get'):
+        with caplog.at_level(logging.DEBUG), mock.patch('requests.Session.get'):
             http.get('https://www.google.com', verify=False)
 
         expected_message = 'An unverified HTTPS request is being made to https://www.google.com'
@@ -228,7 +241,173 @@ def test_fetch_intermediate_certs(self, port):
         with mock.patch('datadog_checks.base.utils.http.create_socket_connection') as mock_create_socket_connection:
             with mock.patch('datadog_checks.base.utils.http.RequestsWrapper.handle_auth_token'):
                 with pytest.raises(SSLError):
-                    with mock.patch('requests.get', side_effect=SSLError):
+                    with mock.patch('requests.Session.get', side_effect=SSLError):
                         http.get('https://localhost:{}'.format(port))
 
         mock_create_socket_connection.assert_called_with('localhost', port)
+
+    def test_fetch_intermediate_certs_tls_ciphers(self):
+        """Test that fetch_intermediate_certs uses the correct ciphers."""
+        instance = {'tls_verify': True, 'tls_ciphers': ['TLS_RSA_WITH_AES_256_GCM_SHA384']}
+        init_config = {}
+        http = RequestsWrapper(instance, init_config)
+
+        with mock.patch('datadog_checks.base.utils.http.create_socket_connection') as mock_create_socket_connection:
+            mock_socket = mock.MagicMock()
+            mock_create_socket_connection.return_value = mock_socket
+
+            with mock.patch('datadog_checks.base.utils.http.ssl.SSLContext') as mock_ssl_context_class:
+                mock_context = mock.MagicMock()
+                mock_ssl_context_class.return_value = mock_context
+
+                # Mock the wrapped socket to avoid actual SSL operations
+                mock_wrapped_socket = mock.MagicMock()
+                mock_context.wrap_socket.return_value.__enter__.return_value = mock_wrapped_socket
+                mock_wrapped_socket.getpeercert.return_value = b'fake_cert_data'
+                mock_wrapped_socket.version.return_value = 'TLSv1.3'
+
+                # Mock the certificate loading to avoid cryptography operations
+                with mock.patch('datadog_checks.base.utils.http.RequestsWrapper.load_intermediate_certs'):
+                    http.fetch_intermediate_certs('example.com', 443)
+
+                # Verify set_ciphers was called with the correct cipher list
+                mock_context.set_ciphers.assert_called_once_with('TLS_RSA_WITH_AES_256_GCM_SHA384')
+
+
+class TestSSLContext:
+    """Test the core SSL context functionality."""
+
+    def test_requests_wrapper_creates_ssl_context(self):
+        """Test that RequestsWrapper creates an SSLContext instance."""
+        instance = {'tls_verify': True}
+        init_config = {}
+        http = RequestsWrapper(instance, init_config)
+
+        assert hasattr(http, 'ssl_context')
+        assert isinstance(http.ssl_context, ssl.SSLContext)
+
+    def test_session_uses_ssl_context_adapter(self):
+        """Test that the session uses SSLContextAdapter for consistent TLS configuration."""
+        instance = {'tls_verify': True}
+        init_config = {}
+        http = RequestsWrapper(instance, init_config)
+
+        session = http.session
+        https_adapter = session.get_adapter('https://example.com')
+
+        assert isinstance(https_adapter, SSLContextAdapter)
+        assert https_adapter.ssl_context is http.ssl_context
+
+    def test_ssl_context_ciphers_can_be_modified(self):
+        """Test that the chosen ciphers can be set on CI runners."""
+        context = ssl.create_default_context()
+        context.set_ciphers('TLS_RSA_WITH_AES_256_GCM_SHA384')
+
+    def test_tls_ciphers_applied_consistently(self):
+        """Test that tls_ciphers are applied consistently."""
+        instance = {'tls_verify': True, 'tls_ciphers': list(IANA_TO_OPENSSL_NAME.keys())}
+        init_config = {}
+        http = RequestsWrapper(instance, init_config)
+
+        # Verify the TLS context wrapper has the cipher configuration
+        assert http.tls_config['tls_ciphers'] == instance['tls_ciphers']
+
+        # Verify the session adapter uses the same TLS context
+        session = http.session
+        https_adapter = session.get_adapter('https://example.com')
+
+        assert isinstance(https_adapter, SSLContextAdapter)
+        assert https_adapter.ssl_context is http.ssl_context
+        # Verify that the ciphers are set correctly in the TLS context
+        for cipher in instance['tls_ciphers']:
+            # At least one entry's name field should match the OpenSSL name
+            assert any(
+                IANA_TO_OPENSSL_NAME.get(cipher) in c.get('name') for c in https_adapter.ssl_context.get_ciphers()
+            )
+
+    def test_default_tls_ciphers(self):
+        """Test that default TLS ciphers are applied when none are specified."""
+        instance = {'tls_verify': True}
+        init_config = {}
+
+        # Mock the SSLContext creation
+        with mock.patch.object(ssl.SSLContext, 'set_ciphers') as mock_set_ciphers:
+            RequestsWrapper(instance, init_config)
+
+            # Verify that the default ciphers are set
+            assert mock_set_ciphers.call_count == 1
+            assert mock_set_ciphers.call_args[0][0] == 'ALL'
+
+    def test_host_header_compatibility(self):
+        """Test that host header functionality works with TLS context unification."""
+        instance = {
+            'tls_use_host_header': True,
+            'headers': {'Host': 'custom-host.example.com'},
+            'tls_verify': True,
+            'tls_ciphers': ['TLS_RSA_WITH_AES_256_GCM_SHA384'],
+        }
+        init_config = {}
+        http = RequestsWrapper(instance, init_config)
+
+        session = http.session
+        https_adapter = session.get_adapter('https://example.com')
+
+        # Should be the combined adapter that supports both TLS context and host headers
+        assert hasattr(https_adapter, 'ssl_context')
+        assert https_adapter.ssl_context is http.ssl_context
+        assert 'SSLContextHostHeaderAdapter' in str(type(https_adapter))
+
+    def test_remapper_functionality_preserved(self):
+        """Test that config remapping functionality is preserved with TLS context unification."""
+        instance = {
+            'disable_ssl_validation': True,
+            'custom_private_key': '/path/to/key.pem',
+        }
+        remapper = {
+            'disable_ssl_validation': {'name': 'tls_verify', 'invert': True},
+            'custom_private_key': {'name': 'tls_private_key'},
+        }
+        init_config = {}
+
+        # Mock the TLS context creation to avoid file operations
+        with mock.patch('datadog_checks.base.utils.http.create_ssl_context') as mock_create_context:
+            mock_context = mock.MagicMock()
+            mock_create_context.return_value = mock_context
+
+            http = RequestsWrapper(instance, init_config, remapper=remapper)
+
+            # Verify remapping worked - disable_ssl_validation: True should become tls_verify: False
+            assert http.tls_config['tls_verify'] is False
+            assert http.tls_config['tls_private_key'] == '/path/to/key.pem'
+
+    def test_backward_compatibility_maintained(self):
+        """Test that all existing TLS configuration options still work."""
+        instance = {
+            'tls_verify': True,
+            'tls_ca_cert': '/path/to/ca.pem',
+            'tls_cert': '/path/to/cert.pem',
+            'tls_private_key': '/path/to/key.pem',
+            'tls_validate_hostname': True,
+            'tls_ignore_warning': False,
+            'tls_protocols_allowed': ['TLSv1.2', 'TLSv1.3'],
+            'tls_ciphers': ['TLS_RSA_WITH_AES_256_GCM_SHA384'],
+        }
+        init_config = {}
+
+        # Mock the TLS context creation to avoid file operations
+        with mock.patch('datadog_checks.base.utils.http.create_ssl_context') as mock_create_context:
+            mock_context = mock.MagicMock()
+            mock_create_context.return_value = mock_context
+
+            # Should not raise any exceptions
+            http = RequestsWrapper(instance, init_config)
+
+            # Verify all options are preserved in RequestsWrapper
+            assert http.options['verify'] == '/path/to/ca.pem'
+            assert http.options['cert'] == ('/path/to/cert.pem', '/path/to/key.pem')
+            assert http.ignore_tls_warning is False
+            assert http.tls_protocols_allowed == ['TLSv1.2', 'TLSv1.3']
+
+            # Verify TLS context wrapper has the right config
+            assert http.tls_config['tls_verify'] is True
+            assert http.tls_config['tls_ciphers'] == ['TLS_RSA_WITH_AES_256_GCM_SHA384']
diff --git a/datadog_checks_dev/datadog_checks/dev/plugin/pytest.py b/datadog_checks_dev/datadog_checks/dev/plugin/pytest.py
index f9eaaf19b38a0..745c0eb69c5e9 100644
--- a/datadog_checks_dev/datadog_checks/dev/plugin/pytest.py
+++ b/datadog_checks_dev/datadog_checks/dev/plugin/pytest.py
@@ -292,7 +292,7 @@ def mock_http_response(mocker):
         from ..http import MockResponse
 
     yield lambda *args, **kwargs: mocker.patch(
-        kwargs.pop('method', 'requests.get'), return_value=MockResponse(*args, **kwargs)
+        kwargs.pop('method', 'requests.Session.get'), return_value=MockResponse(*args, **kwargs)
     )
 
 
diff --git a/datadog_checks_dev/tests/tooling/test_github.py b/datadog_checks_dev/tests/tooling/test_github.py
index ab96b415fcd3e..a5671bcc2c4c8 100644
--- a/datadog_checks_dev/tests/tooling/test_github.py
+++ b/datadog_checks_dev/tests/tooling/test_github.py
@@ -27,7 +27,7 @@ def test_get_pr_approvers(github_response, expected_approvers):
     mock_response.json.return_value = github_response
 
     with mock.patch(
-        "requests.get",
+        "requests.Session.get",
         return_value=mock_response,
     ):
         assert get_pr_approvers("integrations-core", "42", {}) == expected_approvers
diff --git a/datadog_cluster_agent/tests/conftest.py b/datadog_cluster_agent/tests/conftest.py
index 084b6164a174a..4ccf2c30a4710 100644
--- a/datadog_cluster_agent/tests/conftest.py
+++ b/datadog_cluster_agent/tests/conftest.py
@@ -26,7 +26,7 @@ def mock_metrics_endpoint():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/dcgm/tests/conftest.py b/dcgm/tests/conftest.py
index fe3a75dd256b7..ab5c6d305432e 100644
--- a/dcgm/tests/conftest.py
+++ b/dcgm/tests/conftest.py
@@ -45,7 +45,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -59,7 +59,7 @@ def mock_label_remap():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/druid/tests/test_unit.py b/druid/tests/test_unit.py
index ef7ee18b45228..3a21281fbc8bc 100644
--- a/druid/tests/test_unit.py
+++ b/druid/tests/test_unit.py
@@ -22,7 +22,8 @@ def test_missing_url_config(aggregator):
 def test_service_check_can_connect_success(aggregator, instance):
     check = DruidCheck('druid', {}, [instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as req:
+    req = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
         mock_resp = mock.MagicMock(status_code=200)
         mock_resp.json.return_value = {'abc': '123'}
         req.get.return_value = mock_resp
@@ -41,7 +42,8 @@ def test_service_check_can_connect_success(aggregator, instance):
 def test_service_check_can_connect_failure(aggregator, instance, exception_class):
     check = DruidCheck('druid', {}, [instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as req:
+    req = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
         attrs = {'raise_for_status.side_effect': exception_class}
         req.get.side_effect = [mock.MagicMock(status_code=500, **attrs)]
 
diff --git a/ecs_fargate/tests/test_unit.py b/ecs_fargate/tests/test_unit.py
index ed46749111f04..c4f967166bcec 100644
--- a/ecs_fargate/tests/test_unit.py
+++ b/ecs_fargate/tests/test_unit.py
@@ -42,7 +42,7 @@ def test_failing_check(check, aggregator, dd_run_check):
     Testing fargate metadata endpoint error.
     """
     with mock.patch(
-        'datadog_checks.ecs_fargate.ecs_fargate.requests.get', return_value=MockResponse('{}', status_code=500)
+        'datadog_checks.ecs_fargate.ecs_fargate.requests.Session.get', return_value=MockResponse('{}', status_code=500)
     ):
         dd_run_check(check)
 
@@ -55,7 +55,7 @@ def test_invalid_response_check(check, aggregator, dd_run_check):
     Testing invalid fargate metadata payload.
     """
     with mock.patch(
-        'datadog_checks.ecs_fargate.ecs_fargate.requests.get', return_value=MockResponse('{}', status_code=200)
+        'datadog_checks.ecs_fargate.ecs_fargate.requests.Session.get', return_value=MockResponse('{}', status_code=200)
     ):
         dd_run_check(check)
 
@@ -67,7 +67,9 @@ def test_successful_check_linux(check, aggregator, dd_run_check):
     """
     Testing successful fargate check on Linux.
     """
-    with mock.patch('datadog_checks.ecs_fargate.ecs_fargate.requests.get', side_effect=mocked_requests_get_linux):
+    with mock.patch(
+        'datadog_checks.ecs_fargate.ecs_fargate.requests.Session.get', side_effect=mocked_requests_get_linux
+    ):
         with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.get_tags", side_effect=mocked_get_tags):
             with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.c_is_excluded", side_effect=mocked_is_excluded):
                 dd_run_check(check)
@@ -146,7 +148,9 @@ def test_successful_check_windows(check, aggregator, dd_run_check):
     """
     Testing successful fargate check on Windows.
     """
-    with mock.patch('datadog_checks.ecs_fargate.ecs_fargate.requests.get', side_effect=mocked_requests_get_windows):
+    with mock.patch(
+        'datadog_checks.ecs_fargate.ecs_fargate.requests.Session.get', side_effect=mocked_requests_get_windows
+    ):
         with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.get_tags", side_effect=mocked_get_tags):
             with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.c_is_excluded", side_effect=mocked_is_excluded):
                 dd_run_check(check)
@@ -204,7 +208,9 @@ def test_successful_check_wrong_sys_delta(check, aggregator, dd_run_check):
     """
     Testing successful fargate check.
     """
-    with mock.patch('datadog_checks.ecs_fargate.ecs_fargate.requests.get', side_effect=mocked_requests_get_sys_delta):
+    with mock.patch(
+        'datadog_checks.ecs_fargate.ecs_fargate.requests.Session.get', side_effect=mocked_requests_get_sys_delta
+    ):
         with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.get_tags", side_effect=mocked_get_tags):
             with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.c_is_excluded", side_effect=mocked_is_excluded):
                 dd_run_check(check)
@@ -287,7 +293,8 @@ def test_config(test_case, extra_config, expected_http_kwargs, dd_run_check):
     instance = extra_config
     check = FargateCheck('ecs_fargate', {}, instances=[instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200)
 
         dd_run_check(check)
diff --git a/ecs_fargate/tests/test_unit_v4.py b/ecs_fargate/tests/test_unit_v4.py
index d3d3c78703f9c..e7bf70546bfb9 100644
--- a/ecs_fargate/tests/test_unit_v4.py
+++ b/ecs_fargate/tests/test_unit_v4.py
@@ -42,7 +42,9 @@ def test_successful_check_linux_v4(check, aggregator, dd_run_check):
     Testing successful fargate check on Linux on ECS ENDPOINT API v4.
     """
 
-    with mock.patch('datadog_checks.ecs_fargate.ecs_fargate.requests.get', side_effect=mocked_requests_get_linux_v4):
+    with mock.patch(
+        'datadog_checks.ecs_fargate.ecs_fargate.requests.Session.get', side_effect=mocked_requests_get_linux_v4
+    ):
         with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.get_tags", side_effect=mocked_get_tags_v4):
             with mock.patch("datadog_checks.ecs_fargate.ecs_fargate.c_is_excluded", side_effect=mocked_is_excluded):
                 dd_run_check(check)
diff --git a/elastic/tests/test_unit.py b/elastic/tests/test_unit.py
index ce0ca93e21346..551133e47a4fd 100644
--- a/elastic/tests/test_unit.py
+++ b/elastic/tests/test_unit.py
@@ -134,7 +134,7 @@ def test_get_template_metrics(aggregator, instance, mock_http_response):
 
 def test_get_template_metrics_raise_exception(aggregator, instance):
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=MockResponse(status_code=403),
     ):
         check = ESCheck('elastic', {}, instances=[instance])
@@ -151,7 +151,7 @@ def test_get_value_from_path():
 
 def test__get_data_throws_authentication_error(instance):
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=MockResponse(status_code=400),
     ):
         check = ESCheck('elastic', {}, instances=[instance])
@@ -162,7 +162,7 @@ def test__get_data_throws_authentication_error(instance):
 
 def test__get_data_creates_critical_service_alert(aggregator, instance):
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=MockResponse(status_code=500),
     ):
         check = ESCheck('elastic', {}, instances=[instance])
@@ -193,7 +193,7 @@ def test__get_data_creates_critical_service_alert(aggregator, instance):
 )
 def test_disable_legacy_sc_tags(aggregator, es_instance):
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=MockResponse(status_code=500),
     ):
         check = ESCheck('elastic', {}, instances=[es_instance])
diff --git a/envoy/tests/legacy/test_unit.py b/envoy/tests/legacy/test_unit.py
index 0f76041d1a618..f0c6a19ad38f8 100644
--- a/envoy/tests/legacy/test_unit.py
+++ b/envoy/tests/legacy/test_unit.py
@@ -139,7 +139,8 @@ def test_config(extra_config, expected_http_kwargs, check, dd_run_check):
     instance.update(extra_config)
     check = check(instance)
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200)
 
         dd_run_check(check)
@@ -189,7 +190,7 @@ def test_metadata_with_exception(
     check.check_id = 'test:123'
     check.log = mock.MagicMock()
 
-    with mock.patch('requests.get', side_effect=exception):
+    with mock.patch('requests.Session.get', side_effect=exception):
         check._collect_metadata()
         datadog_agent.assert_metadata_count(0)
         check.log.warning.assert_called_with(*log_call_parameters)
diff --git a/etcd/tests/test_integration.py b/etcd/tests/test_integration.py
index 734bd86b67da7..da94be9a527c3 100644
--- a/etcd/tests/test_integration.py
+++ b/etcd/tests/test_integration.py
@@ -78,7 +78,8 @@ def test_config(instance, test_case, extra_config, expected_http_kwargs, dd_run_
     instance.update(extra_config)
     check = Etcd(CHECK_NAME, {}, [instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200)
 
         dd_run_check(check)
diff --git a/external_dns/tests/conftest.py b/external_dns/tests/conftest.py
index 48e4c325e9ec8..659cb475e7f29 100644
--- a/external_dns/tests/conftest.py
+++ b/external_dns/tests/conftest.py
@@ -19,7 +19,7 @@ def mock_external_dns():
         text_data = f.read()
 
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split('\n'), headers={'Content-Type': 'text/plain'}
         ),
diff --git a/fluxcd/tests/conftest.py b/fluxcd/tests/conftest.py
index 2b43fc5bca29e..55a944c2d90bd 100644
--- a/fluxcd/tests/conftest.py
+++ b/fluxcd/tests/conftest.py
@@ -76,7 +76,7 @@ def mock_metrics_v1():
         content = f.read()
 
     with mock.patch(
-        "requests.get",
+        "requests.Session.get",
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: content.split("\n"),
@@ -94,7 +94,7 @@ def mock_metrics_v2():
         content = f.read()
 
     with mock.patch(
-        "requests.get",
+        "requests.Session.get",
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: content.split("\n"),
diff --git a/fly_io/tests/conftest.py b/fly_io/tests/conftest.py
index beeb4fefe4628..7c49e6c751932 100644
--- a/fly_io/tests/conftest.py
+++ b/fly_io/tests/conftest.py
@@ -128,5 +128,5 @@ def get(url, *args, **kwargs):
         return mock.MagicMock(json=mock_json, status_code=mock_status_code)
 
     mock_get = mock.MagicMock(side_effect=get)
-    monkeypatch.setattr('requests.get', mock_get)
+    monkeypatch.setattr('requests.Session.get', mock_get)
     return mock_get
diff --git a/gitlab/tests/conftest.py b/gitlab/tests/conftest.py
index 9b8ce8222338c..b0d47e010b803 100644
--- a/gitlab/tests/conftest.py
+++ b/gitlab/tests/conftest.py
@@ -104,7 +104,7 @@ def dd_environment():
 @pytest.fixture()
 def mock_data():
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         side_effect=mocked_requests_get,
     ):
         yield
diff --git a/gitlab_runner/tests/test_unit.py b/gitlab_runner/tests/test_unit.py
index 4d44c97dd137e..9d3fb039050aa 100644
--- a/gitlab_runner/tests/test_unit.py
+++ b/gitlab_runner/tests/test_unit.py
@@ -28,7 +28,8 @@ def test_timeout(test_case, timeout_config, expected_timeout):
 
     gitlab_runner = GitlabRunnerCheck('gitlab_runner', common.CONFIG['init_config'], instances=config['instances'])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200)
 
         gitlab_runner.check(config['instances'][0])
diff --git a/haproxy/tests/conftest.py b/haproxy/tests/conftest.py
index b72ae7fc1806f..c4b3be16cc61e 100644
--- a/haproxy/tests/conftest.py
+++ b/haproxy/tests/conftest.py
@@ -210,7 +210,7 @@ def haproxy_mock():
     filepath = os.path.join(HERE, 'fixtures', 'mock_data')
     with open(filepath, 'rb') as f:
         data = f.read()
-    p = mock.patch('requests.get', return_value=mock.Mock(content=data))
+    p = mock.patch('requests.Session.get', return_value=mock.Mock(content=data))
     yield p.start()
     p.stop()
 
@@ -228,7 +228,7 @@ def haproxy_mock_evil():
     filepath = os.path.join(HERE, 'fixtures', 'mock_data_evil')
     with open(filepath, 'rb') as f:
         data = f.read()
-    p = mock.patch('requests.get', return_value=mock.Mock(content=data))
+    p = mock.patch('requests.Session.get', return_value=mock.Mock(content=data))
     yield p.start()
     p.stop()
 
@@ -238,7 +238,7 @@ def haproxy_mock_enterprise_version_info():
     filepath = os.path.join(HERE, 'fixtures', 'enterprise_version_info.html')
     with open(filepath, 'rb') as f:
         data = f.read()
-    with mock.patch('requests.get', return_value=mock.Mock(content=data)) as p:
+    with mock.patch('requests.Session.get', return_value=mock.Mock(content=data)) as p:
         yield p
 
 
diff --git a/haproxy/tests/legacy/test_unit.py b/haproxy/tests/legacy/test_unit.py
index b7edf8efc7f48..f93fca547f5ce 100644
--- a/haproxy/tests/legacy/test_unit.py
+++ b/haproxy/tests/legacy/test_unit.py
@@ -433,7 +433,7 @@ def test_version_failure(aggregator, check, datadog_agent):
     filepath = os.path.join(os.path.dirname(common.HERE), 'fixtures', 'mock_data')
     with open(filepath, 'rb') as f:
         data = f.read()
-    with mock.patch('requests.get') as m:
+    with mock.patch('requests.Session.get') as m:
         m.side_effect = [RuntimeError("Ooops"), mock.Mock(content=data)]
         haproxy_check.check(config)
 
diff --git a/harbor/tests/conftest.py b/harbor/tests/conftest.py
index ea2a80f91a529..65fffa87bd2ca 100644
--- a/harbor/tests/conftest.py
+++ b/harbor/tests/conftest.py
@@ -107,7 +107,7 @@ def harbor_api(harbor_check, admin_instance, patch_requests):
 
 @pytest.fixture
 def patch_requests():
-    with patch("requests.api.request", side_effect=mocked_requests):
+    with patch("requests.Session.request", side_effect=mocked_requests):
         yield
 
 
@@ -117,32 +117,32 @@ def get_docker_compose_file():
     return os.path.join(HERE, 'compose', harbor_folder, 'docker-compose.yml')
 
 
-def mocked_requests(_, *args, **kwargs):
+def mocked_requests(_, url, **kwargs):
     def match(url, *candidates_url):
         for c in candidates_url:
             if url == c.format(base_url=URL):
                 return True
         return False
 
-    if match(args[0], LOGIN_URL):
+    if match(url, LOGIN_URL):
         return MockResponse()
-    elif match(args[0], HEALTH_URL):
+    elif match(url, HEALTH_URL):
         return MockResponse(json_data=HEALTH_FIXTURE)
-    elif match(args[0], PING_URL):
+    elif match(url, PING_URL):
         return MockResponse('Pong')
-    elif match(args[0], CHARTREPO_HEALTH_URL):
+    elif match(url, CHARTREPO_HEALTH_URL):
         return MockResponse(json_data=CHARTREPO_HEALTH_FIXTURE)
-    elif match(args[0], PROJECTS_URL):
+    elif match(url, PROJECTS_URL):
         return MockResponse(json_data=PROJECTS_FIXTURE)
-    elif match(args[0], REGISTRIES_URL):
+    elif match(url, REGISTRIES_URL):
         return MockResponse(json_data=REGISTRIES_FIXTURE)
-    elif match(args[0], REGISTRIES_PING_URL):
+    elif match(url, REGISTRIES_PING_URL):
         return MockResponse()
-    elif match(args[0], VOLUME_INFO_URL):
+    elif match(url, VOLUME_INFO_URL):
         if HARBOR_VERSION < VERSION_2_2:
             return MockResponse(json_data=VOLUME_INFO_PRE_2_2_FIXTURE)
         return MockResponse(json_data=VOLUME_INFO_FIXTURE)
-    elif match(args[0], SYSTEM_INFO_URL):
+    elif match(url, SYSTEM_INFO_URL):
         return MockResponse(json_data=SYSTEM_INFO_FIXTURE)
 
     return MockResponse(status_code=404)
diff --git a/hdfs_datanode/tests/conftest.py b/hdfs_datanode/tests/conftest.py
index 48b97b46c3a53..d8248b94a20a1 100644
--- a/hdfs_datanode/tests/conftest.py
+++ b/hdfs_datanode/tests/conftest.py
@@ -37,19 +37,19 @@ def instance():
 
 @pytest.fixture
 def mocked_request():
-    with patch('requests.get', new=requests_get_mock):
+    with patch('requests.Session.get', new=requests_get_mock):
         yield
 
 
 @pytest.fixture
 def mocked_metadata_request():
-    with patch('requests.get', new=requests_metadata_mock):
+    with patch('requests.Session.get', new=requests_metadata_mock):
         yield
 
 
 @pytest.fixture
 def mocked_auth_request():
-    with patch('requests.get', new=requests_auth_mock):
+    with patch('requests.Session.get', new=requests_auth_mock):
         yield
 
 
diff --git a/hdfs_namenode/tests/conftest.py b/hdfs_namenode/tests/conftest.py
index 47d43f92010d0..f6a0da366dfab 100644
--- a/hdfs_namenode/tests/conftest.py
+++ b/hdfs_namenode/tests/conftest.py
@@ -44,17 +44,17 @@ def check():
 
 @pytest.fixture
 def mocked_request():
-    with patch("requests.get", new=requests_get_mock):
+    with patch("requests.Session.get", new=requests_get_mock):
         yield
 
 
 @pytest.fixture
 def mocked_auth_request():
-    with patch("requests.get", new=requests_auth_mock):
+    with patch("requests.Session.get", new=requests_auth_mock):
         yield
 
 
-def requests_get_mock(url, *args, **kwargs):
+def requests_get_mock(session, url, *args, **kwargs):
     if url == NAME_SYSTEM_STATE_URL:
         return MockResponse(file_path=os.path.join(FIXTURE_DIR, 'hdfs_namesystem_state.json'))
     elif url == NAME_SYSTEM_URL:
diff --git a/http_check/tests/test_http_integration.py b/http_check/tests/test_http_integration.py
index 4ccbc5c601e7b..079bed7b8fd5a 100644
--- a/http_check/tests/test_http_integration.py
+++ b/http_check/tests/test_http_integration.py
@@ -432,7 +432,7 @@ def test_data_methods(aggregator, http_check):
         aggregator.reset()
 
 
-def test_unexisting_ca_cert_should_throw_error(aggregator, dd_run_check):
+def test_unexisting_ca_cert_should_log_warning(aggregator, dd_run_check):
     instance = {
         'name': 'Test Web VM HTTPS SSL',
         'url': 'https://foo.bar.net/',
@@ -445,10 +445,11 @@ def test_unexisting_ca_cert_should_throw_error(aggregator, dd_run_check):
     }
 
     check = HTTPCheck('http_check', {'ca_certs': 'foo'}, [instance])
+    with mock.patch('datadog_checks.base.utils.http.logging.Logger.warning') as mock_warning:
 
-    dd_run_check(check)
-    aggregator.assert_service_check(HTTPCheck.SC_STATUS, status=AgentCheck.CRITICAL)
-    assert 'invalid path: /tmp/unexisting.crt' in aggregator._service_checks[HTTPCheck.SC_STATUS][0].message
+        dd_run_check(check)
+        mock_warning.assert_called_once()
+        assert any(instance['tls_ca_cert'] in arg for arg in mock_warning.call_args)
 
 
 def test_instance_auth_token(dd_run_check):
diff --git a/impala/tests/conftest.py b/impala/tests/conftest.py
index 5aa771d5e50de..c20b489212e17 100644
--- a/impala/tests/conftest.py
+++ b/impala/tests/conftest.py
@@ -101,7 +101,7 @@ def mock_metrics(request):
         content = fixture_file.read()
 
     with mock.patch(
-        "requests.get",
+        "requests.Session.get",
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: content.split("\n"),
diff --git a/kube_apiserver_metrics/tests/test_kube_apiserver_metrics_1_25.py b/kube_apiserver_metrics/tests/test_kube_apiserver_metrics_1_25.py
index afec1846bb1d5..b1ff0388c4741 100644
--- a/kube_apiserver_metrics/tests/test_kube_apiserver_metrics_1_25.py
+++ b/kube_apiserver_metrics/tests/test_kube_apiserver_metrics_1_25.py
@@ -25,7 +25,7 @@ def mock_get():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: text_data.split("\n"),
diff --git a/kube_apiserver_metrics/tests/test_sli_metrics.py b/kube_apiserver_metrics/tests/test_sli_metrics.py
index d3a726bb592c4..b550165a81955 100644
--- a/kube_apiserver_metrics/tests/test_sli_metrics.py
+++ b/kube_apiserver_metrics/tests/test_sli_metrics.py
@@ -22,7 +22,7 @@ def mock_metrics():
     with open(f_name, "r") as f:
         text_data = f.read()
     with mock.patch(
-        "requests.get",
+        "requests.Session.get",
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: text_data.split("\n"),
diff --git a/kube_controller_manager/tests/test_kube_controller_manager.py b/kube_controller_manager/tests/test_kube_controller_manager.py
index 7a16d6665e847..4c4ac8ceaf4e3 100644
--- a/kube_controller_manager/tests/test_kube_controller_manager.py
+++ b/kube_controller_manager/tests/test_kube_controller_manager.py
@@ -37,7 +37,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -146,13 +146,13 @@ def test_service_check_ok(monkeypatch):
     ]
 
     # successful health check
-    with mock.patch("requests.get", return_value=mock.MagicMock(status_code=200)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(status_code=200)):
         check._perform_service_check(instance)
 
     # failed health check
     raise_error = mock.Mock()
     raise_error.side_effect = requests.HTTPError('health check failed')
-    with mock.patch("requests.get", return_value=mock.MagicMock(raise_for_status=raise_error)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(raise_for_status=raise_error)):
         check._perform_service_check(instance)
 
     check.service_check.assert_has_calls(calls)
diff --git a/kube_controller_manager/tests/test_sli_metrics.py b/kube_controller_manager/tests/test_sli_metrics.py
index c3ff350c550ef..420e7255ce8e2 100644
--- a/kube_controller_manager/tests/test_sli_metrics.py
+++ b/kube_controller_manager/tests/test_sli_metrics.py
@@ -22,7 +22,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -205,7 +205,7 @@ def mock_request():
 
 
 def test_detect_sli_endpoint(mock_metrics, instance):
-    with mock.patch('requests.get') as mock_request:
+    with mock.patch('requests.Session.get') as mock_request:
         mock_request.return_value.status_code = 200
         c = KubeControllerManagerCheck(CHECK_NAME, {}, [instance])
         c.check(instance)
@@ -213,7 +213,7 @@ def test_detect_sli_endpoint(mock_metrics, instance):
 
 
 def test_detect_sli_endpoint_404(mock_metrics, instance):
-    with mock.patch('requests.get') as mock_request:
+    with mock.patch('requests.Session.get') as mock_request:
         mock_request.return_value.status_code = 404
         c = KubeControllerManagerCheck(CHECK_NAME, {}, [instance])
         c.check(instance)
@@ -221,7 +221,7 @@ def test_detect_sli_endpoint_404(mock_metrics, instance):
 
 
 def test_detect_sli_endpoint_403(mock_metrics, mock_request, instance):
-    with mock.patch('requests.get') as mock_request:
+    with mock.patch('requests.Session.get') as mock_request:
         mock_request.return_value.status_code = 403
         c = KubeControllerManagerCheck(CHECK_NAME, {}, [instance])
         c.check(instance)
diff --git a/kube_dns/tests/test_kube_dns.py b/kube_dns/tests/test_kube_dns.py
index 6b92c0089388c..dcb44c2df6efd 100644
--- a/kube_dns/tests/test_kube_dns.py
+++ b/kube_dns/tests/test_kube_dns.py
@@ -24,7 +24,7 @@ def mock_get():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -96,13 +96,13 @@ def test_service_check_ok(self, monkeypatch):
         ]
 
         # successful health check
-        with mock.patch("requests.get", return_value=mock.MagicMock(status_code=200)):
+        with mock.patch('requests.Session.get', return_value=mock.MagicMock(status_code=200)):
             check._perform_service_check(instance)
 
         # failed health check
         raise_error = mock.Mock()
         raise_error.side_effect = requests.HTTPError('health check failed')
-        with mock.patch("requests.get", return_value=mock.MagicMock(raise_for_status=raise_error)):
+        with mock.patch('requests.Session.get', return_value=mock.MagicMock(raise_for_status=raise_error)):
             check._perform_service_check(instance)
 
         check.service_check.assert_has_calls(calls)
diff --git a/kube_metrics_server/tests/test_kube_metrics_server.py b/kube_metrics_server/tests/test_kube_metrics_server.py
index 96fea70a8ea66..4453dabbba072 100644
--- a/kube_metrics_server/tests/test_kube_metrics_server.py
+++ b/kube_metrics_server/tests/test_kube_metrics_server.py
@@ -28,7 +28,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -76,13 +76,13 @@ def test_service_check_ok(monkeypatch):
     ]
 
     # successful health check
-    with mock.patch("requests.get", return_value=mock.MagicMock(status_code=200)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(status_code=200)):
         check._perform_service_check(instance)
 
     # failed health check
     raise_error = mock.Mock()
     raise_error.side_effect = requests.HTTPError('health check failed')
-    with mock.patch("requests.get", return_value=mock.MagicMock(raise_for_status=raise_error)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(raise_for_status=raise_error)):
         check._perform_service_check(instance)
 
     check.service_check.assert_has_calls(calls)
diff --git a/kube_proxy/tests/test_kube_proxy.py b/kube_proxy/tests/test_kube_proxy.py
index 941d6dbe4da83..c31b02b722f32 100644
--- a/kube_proxy/tests/test_kube_proxy.py
+++ b/kube_proxy/tests/test_kube_proxy.py
@@ -25,7 +25,7 @@ def mock_iptables():
     with open(f_name, 'r') as f:
         text_data = f.read()
     mock_iptables = mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -40,7 +40,7 @@ def mock_userspace():
     with open(f_name, 'r') as f:
         text_data = f.read()
     mock_userspace = mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -119,13 +119,13 @@ def test_service_check_ok(monkeypatch):
     ]
 
     # successful health check
-    with mock.patch("requests.get", return_value=mock.MagicMock(status_code=200)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(status_code=200)):
         check._perform_service_check(instance)
 
     # failed health check
     raise_error = mock.Mock()
     raise_error.side_effect = requests.HTTPError('health check failed')
-    with mock.patch("requests.get", return_value=mock.MagicMock(raise_for_status=raise_error)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(raise_for_status=raise_error)):
         check._perform_service_check(instance)
 
     check.service_check.assert_has_calls(calls)
diff --git a/kube_proxy/tests/test_kube_proxy_1_21_1.py b/kube_proxy/tests/test_kube_proxy_1_21_1.py
index 925bf54ee78c1..51eaddfbac5b6 100644
--- a/kube_proxy/tests/test_kube_proxy_1_21_1.py
+++ b/kube_proxy/tests/test_kube_proxy_1_21_1.py
@@ -22,7 +22,7 @@ def mock_iptables():
     with open(f_name, 'r') as f:
         text_data = f.read()
     mock_iptables = mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -37,7 +37,7 @@ def mock_userspace():
     with open(f_name, 'r') as f:
         text_data = f.read()
     mock_userspace = mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/kube_scheduler/tests/test_kube_scheduler_1_13.py b/kube_scheduler/tests/test_kube_scheduler_1_13.py
index ac60b73837462..e7ae1df38bf1a 100644
--- a/kube_scheduler/tests/test_kube_scheduler_1_13.py
+++ b/kube_scheduler/tests/test_kube_scheduler_1_13.py
@@ -23,7 +23,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/kube_scheduler/tests/test_kube_scheduler_1_14.py b/kube_scheduler/tests/test_kube_scheduler_1_14.py
index 4f6e4bfb75eaf..03b6ae525e03b 100644
--- a/kube_scheduler/tests/test_kube_scheduler_1_14.py
+++ b/kube_scheduler/tests/test_kube_scheduler_1_14.py
@@ -25,7 +25,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -118,13 +118,13 @@ def test_service_check_ok(monkeypatch):
     ]
 
     # successful health check
-    with mock.patch("requests.get", return_value=mock.MagicMock(status_code=200)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(status_code=200)):
         check._perform_service_check(instance)
 
     # failed health check
     raise_error = mock.Mock()
     raise_error.side_effect = requests.HTTPError('health check failed')
-    with mock.patch("requests.get", return_value=mock.MagicMock(raise_for_status=raise_error)):
+    with mock.patch('requests.Session.get', return_value=mock.MagicMock(raise_for_status=raise_error)):
         check._perform_service_check(instance)
 
     check.service_check.assert_has_calls(calls)
diff --git a/kube_scheduler/tests/test_kube_scheduler_1_23.py b/kube_scheduler/tests/test_kube_scheduler_1_23.py
index 6ea03cbe2e17d..4e97823166a79 100644
--- a/kube_scheduler/tests/test_kube_scheduler_1_23.py
+++ b/kube_scheduler/tests/test_kube_scheduler_1_23.py
@@ -23,7 +23,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/kube_scheduler/tests/test_kube_scheduler_1_26.py b/kube_scheduler/tests/test_kube_scheduler_1_26.py
index 853f7a7072bf7..0655cc65558cd 100644
--- a/kube_scheduler/tests/test_kube_scheduler_1_26.py
+++ b/kube_scheduler/tests/test_kube_scheduler_1_26.py
@@ -22,7 +22,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/kube_scheduler/tests/test_kube_scheduler_1_29.py b/kube_scheduler/tests/test_kube_scheduler_1_29.py
index 01ec0d749e391..16fe535ce6816 100644
--- a/kube_scheduler/tests/test_kube_scheduler_1_29.py
+++ b/kube_scheduler/tests/test_kube_scheduler_1_29.py
@@ -22,7 +22,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/kube_scheduler/tests/test_sli_metrics.py b/kube_scheduler/tests/test_sli_metrics.py
index 706050f730f43..dd98007f4e9d8 100644
--- a/kube_scheduler/tests/test_sli_metrics.py
+++ b/kube_scheduler/tests/test_sli_metrics.py
@@ -22,7 +22,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
@@ -97,7 +97,7 @@ def mock_request():
 
 
 def test_detect_sli_endpoint(mock_metrics, instance):
-    with mock.patch('requests.get') as mock_request:
+    with mock.patch('requests.Session.get') as mock_request:
         mock_request.return_value.status_code = 200
         c = KubeSchedulerCheck(CHECK_NAME, {}, [instance])
         c.check(instance)
@@ -105,7 +105,7 @@ def test_detect_sli_endpoint(mock_metrics, instance):
 
 
 def test_detect_sli_endpoint_404(mock_metrics, instance):
-    with mock.patch('requests.get') as mock_request:
+    with mock.patch('requests.Session.get') as mock_request:
         mock_request.return_value.status_code = 404
         c = KubeSchedulerCheck(CHECK_NAME, {}, [instance])
         c.check(instance)
@@ -113,7 +113,7 @@ def test_detect_sli_endpoint_404(mock_metrics, instance):
 
 
 def test_detect_sli_endpoint_403(mock_metrics, instance):
-    with mock.patch('requests.get') as mock_request:
+    with mock.patch('requests.Session.get') as mock_request:
         mock_request.return_value.status_code = 403
         c = KubeSchedulerCheck(CHECK_NAME, {}, [instance])
         c.check(instance)
diff --git a/kubelet/tests/test_kubelet.py b/kubelet/tests/test_kubelet.py
index 4328df2671443..ea344afbcdc46 100644
--- a/kubelet/tests/test_kubelet.py
+++ b/kubelet/tests/test_kubelet.py
@@ -563,7 +563,7 @@ def test_kubelet_credentials_update(monkeypatch, aggregator):
     get = mock.MagicMock(
         status_code=200, iter_lines=lambda **kwargs: mock_from_file('kubelet_metrics_1_14.txt').splitlines()
     )
-    with mock.patch('requests.get', return_value=get):
+    with mock.patch('requests.Session.get', return_value=get):
         check.check(instance)
 
     assert check._http_handlers[instance['kubelet_metrics_endpoint']].options['verify'] is True
@@ -573,7 +573,7 @@ def test_kubelet_credentials_update(monkeypatch, aggregator):
         status_code=200, iter_lines=lambda **kwargs: mock_from_file('kubelet_metrics_1_14.txt').splitlines()
     )
     kubelet_conn_info = {'url': 'http://127.0.0.1:10255', 'ca_cert': False}
-    with mock.patch('requests.get', return_value=get), mock.patch(
+    with mock.patch('requests.Session.get', return_value=get), mock.patch(
         'datadog_checks.kubelet.kubelet.get_connection_info', return_value=kubelet_conn_info
     ):
         check.check(instance)
@@ -1049,7 +1049,7 @@ def test_perform_kubelet_check(monkeypatch):
 
     instance_tags = ["one:1"]
     get = MockedResponse()
-    with mock.patch("requests.get", side_effect=get):
+    with mock.patch('requests.Session.get', side_effect=get):
         check._perform_kubelet_check(instance_tags)
 
     get.assert_has_calls(
@@ -1093,7 +1093,7 @@ def test_report_node_metrics_kubernetes1_18(monkeypatch, aggregator):
 
     get = mock.MagicMock(status_code=404, iter_lines=lambda **kwargs: "Error Code")
     get.raise_for_status.side_effect = requests.HTTPError('error')
-    with mock.patch('requests.get', return_value=get):
+    with mock.patch('requests.Session.get', return_value=get):
         check._report_node_metrics(['foo:bar'])
         aggregator.assert_all_metrics_covered()
 
diff --git a/kubevirt_api/tests/test_unit.py b/kubevirt_api/tests/test_unit.py
index 2324214c30057..1a4b040e86d05 100644
--- a/kubevirt_api/tests/test_unit.py
+++ b/kubevirt_api/tests/test_unit.py
@@ -18,7 +18,7 @@
 
 
 def test_check_collects_all_metrics(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     check = KubeVirtApiCheck("kubevirt_api", {}, [instance])
 
@@ -95,7 +95,7 @@ def test_check_collects_all_metrics(dd_run_check, aggregator, instance, mocker):
 
 
 def test_check_sends_zero_count_for_vms(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     check = KubeVirtApiCheck("kubevirt_api", {}, [instance])
 
@@ -116,7 +116,7 @@ def test_check_sends_zero_count_for_vms(dd_run_check, aggregator, instance, mock
 
 
 def test_check_sends_zero_count_for_vmis(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     check = KubeVirtApiCheck("kubevirt_api", {}, [instance])
 
@@ -154,7 +154,7 @@ def test_emits_zero_can_connect_when_service_is_down(dd_run_check, aggregator, i
 
 
 def test_emits_one_can_connect_when_service_is_up(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     check = KubeVirtApiCheck("kubevirt_api", {}, [instance])
     check._setup_kube_client = lambda: None
@@ -171,7 +171,7 @@ def test_emits_one_can_connect_when_service_is_up(dd_run_check, aggregator, inst
 
 
 def test_raise_exception_when_metrics_endpoint_is_bad(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     check = KubeVirtApiCheck("kubevirt_api", {}, [BAD_METRICS_HOSTNAME_INSTANCE])
     check._setup_kube_client = lambda: None
@@ -190,7 +190,7 @@ def test_raise_exception_when_metrics_endpoint_is_bad(dd_run_check, aggregator,
 
 
 def test_raise_exception_cannot_connect_to_kubernetes_api(dd_run_check, aggregator, instance, mocker, caplog):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     check = KubeVirtApiCheck("kubevirt_api", {}, [instance])
     with pytest.raises(
@@ -202,7 +202,7 @@ def test_raise_exception_cannot_connect_to_kubernetes_api(dd_run_check, aggregat
 
 
 def test_log_warning_healthz_endpoint_not_provided(dd_run_check, aggregator, instance, mocker, caplog):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     new_instance = deepcopy(instance)
     new_instance.pop("kubevirt_api_healthz_endpoint")
diff --git a/kubevirt_controller/tests/test_unit.py b/kubevirt_controller/tests/test_unit.py
index 50cd1fd3fe596..0a6bcb988a40c 100644
--- a/kubevirt_controller/tests/test_unit.py
+++ b/kubevirt_controller/tests/test_unit.py
@@ -16,7 +16,7 @@
 
 
 def test_emits_can_connect_one_when_service_is_up(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     check = KubeVirtControllerCheck("kubevirt_controller", {}, [instance])
     dd_run_check(check)
     aggregator.assert_metric(
@@ -36,7 +36,7 @@ def test_emits_can_connect_zero_when_service_is_down(dd_run_check, aggregator, i
 
 
 def test_check_collects_all_metrics(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
 
     check = KubeVirtControllerCheck("kubevirt_controller", {}, [instance])
 
diff --git a/kubevirt_handler/tests/test_unit.py b/kubevirt_handler/tests/test_unit.py
index feb3121468339..01e8e42c4a9ba 100644
--- a/kubevirt_handler/tests/test_unit.py
+++ b/kubevirt_handler/tests/test_unit.py
@@ -17,7 +17,7 @@
 
 
 def test_check_collects_metrics(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     check = KubeVirtHandlerCheck("kubevirt_handler", {}, [instance])
     dd_run_check(check)
 
@@ -122,7 +122,7 @@ def test_check_collects_metrics(dd_run_check, aggregator, instance, mocker):
 
 
 def test_logs_warning_when_healthz_endpoint_is_missing(dd_run_check, aggregator, instance, mocker, caplog):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     del instance["kubevirt_handler_healthz_endpoint"]
     check = KubeVirtHandlerCheck("kubevirt_handler", {}, [instance])
     dd_run_check(check)
@@ -134,7 +134,7 @@ def test_logs_warning_when_healthz_endpoint_is_missing(dd_run_check, aggregator,
 
 
 def test_emits_can_connect_one_when_service_is_up(dd_run_check, aggregator, instance, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     check = KubeVirtHandlerCheck("kubevirt_handler", {}, [instance])
     dd_run_check(check)
     aggregator.assert_metric(
@@ -157,7 +157,7 @@ def test_emits_can_connect_zero_when_service_is_down(dd_run_check, aggregator, i
 
 
 def test_version_metadata(instance, dd_run_check, datadog_agent, aggregator, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     check = KubeVirtHandlerCheck("kubevirt_handler", {}, [instance])
     check.check_id = "test:123"
     dd_run_check(check)
diff --git a/mapreduce/tests/conftest.py b/mapreduce/tests/conftest.py
index 087f9adc5b68b..dea2ab20b4951 100644
--- a/mapreduce/tests/conftest.py
+++ b/mapreduce/tests/conftest.py
@@ -52,13 +52,13 @@ def instance():
 
 @pytest.fixture
 def mocked_request():
-    with patch("requests.get", new=requests_get_mock):
+    with patch("requests.Session.get", new=requests_get_mock):
         yield
 
 
 @pytest.fixture
 def mocked_auth_request():
-    with patch("requests.get", new=requests_auth_mock):
+    with patch("requests.Session.get", new=requests_auth_mock):
         yield
 
 
@@ -66,7 +66,7 @@ def get_custom_hosts():
     return [(host, '127.0.0.1') for host in MOCKED_E2E_HOSTS]
 
 
-def requests_get_mock(*args, **kwargs):
+def requests_get_mock(session, *args, **kwargs):
     url = args[0]
     # The parameter that creates the query params (kwargs) is an unordered dict,
     #   so the query params can be in any order
@@ -94,7 +94,7 @@ def requests_get_mock(*args, **kwargs):
     raise Exception("There is no mock request for {}".format(url))
 
 
-def requests_auth_mock(*args, **kwargs):
+def requests_auth_mock(session, *args, **kwargs):
     # Make sure we're passing in authentication
     assert 'auth' in kwargs, "Error, missing authentication"
 
@@ -102,4 +102,4 @@ def requests_auth_mock(*args, **kwargs):
     assert kwargs['auth'] == (TEST_USERNAME, TEST_PASSWORD), "Incorrect username or password"
 
     # Return mocked request.get(...)
-    return requests_get_mock(*args, **kwargs)
+    return requests_get_mock(session, *args, **kwargs)
diff --git a/marathon/tests/test_unit.py b/marathon/tests/test_unit.py
index 4c39a7afe3be3..ef104e6264e90 100644
--- a/marathon/tests/test_unit.py
+++ b/marathon/tests/test_unit.py
@@ -107,7 +107,8 @@ def test_config(test_case, init_config, extra_config, expected_http_kwargs):
     instance.update(extra_config)
     check = Marathon('marathon', init_config, instances=[instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200)
 
         check.check(instance)
diff --git a/mesos_master/tests/test_check.py b/mesos_master/tests/test_check.py
index 721acce7a3613..4c026dcabc9c2 100644
--- a/mesos_master/tests/test_check.py
+++ b/mesos_master/tests/test_check.py
@@ -152,7 +152,8 @@ def test_can_connect_service_check(
 ):
     check = MesosMaster('mesos_master', {}, [instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.side_effect = request_mock_side_effects
 
         try:
diff --git a/mesos_slave/tests/test_unit.py b/mesos_slave/tests/test_unit.py
index 0cc7b699b6d96..098e3683313cf 100644
--- a/mesos_slave/tests/test_unit.py
+++ b/mesos_slave/tests/test_unit.py
@@ -180,7 +180,8 @@ def test_can_connect_service_check_state(
     instance, aggregator, test_case_name, request_mock_effects, expected_tags, expect_exception, expected_status
 ):
     check = MesosSlave('mesos_slave', {}, [instance])
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.side_effect = request_mock_effects
         try:
             check._process_state_info('http://hello.com', instance['tasks'], 5050, instance['tags'])
@@ -198,7 +199,8 @@ def test_can_connect_service_with_instance_cluster_name(instance, aggregator):
     expected_tags = ['url:http://hello.com/state'] + cluster_name_tag + additional_tags
     expected_status = AgentCheck.OK
     check = MesosSlave('mesos_slave', {}, [instance])
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.side_effect = [mock.MagicMock(status_code=200, content='{}')]
         try:
             check._process_state_info('http://hello.com', instance['tasks'], 5050, instance['tags'])
@@ -216,7 +218,8 @@ def test_can_connect_service_check_stats(
     instance, aggregator, test_case_name, request_mock_effects, expected_tags, expect_exception, expected_status
 ):
     check = MesosSlave('mesos_slave', {}, [instance])
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.side_effect = request_mock_effects
         try:
             check._process_stats_info('http://hello.com', instance['tags'])
diff --git a/nginx/tests/test_unit.py b/nginx/tests/test_unit.py
index 27e29dfcad00d..6209431250387 100644
--- a/nginx/tests/test_unit.py
+++ b/nginx/tests/test_unit.py
@@ -71,7 +71,8 @@ def test_config(check, instance, test_case, extra_config, expected_http_kwargs):
 
     c = check(instance)
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200, content=b'{}')
 
         c.check(instance)
@@ -93,7 +94,8 @@ def test_config(check, instance, test_case, extra_config, expected_http_kwargs):
 def test_no_version(check, instance, caplog):
     c = check(instance)
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200, content=b'{}', headers={'server': 'nginx'})
 
         c.check(instance)
diff --git a/nginx/tests/test_vts.py b/nginx/tests/test_vts.py
index 696f8498c397a..8a06abe7b5b5e 100644
--- a/nginx/tests/test_vts.py
+++ b/nginx/tests/test_vts.py
@@ -49,7 +49,7 @@ def test_vts(check, instance_vts, aggregator):
 
 @pytest.mark.unit
 def test_vts_unit(dd_run_check, aggregator, mocked_instance_vts, check, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     c = check(mocked_instance_vts)
     dd_run_check(c)
 
diff --git a/nginx_ingress_controller/tests/test_nginx_ingress_controller.py b/nginx_ingress_controller/tests/test_nginx_ingress_controller.py
index 8066617d61bc5..5ac427b270c62 100644
--- a/nginx_ingress_controller/tests/test_nginx_ingress_controller.py
+++ b/nginx_ingress_controller/tests/test_nginx_ingress_controller.py
@@ -21,7 +21,7 @@ def mock_data():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/nvidia_nim/tests/test_unit.py b/nvidia_nim/tests/test_unit.py
index 980580e11fab3..deaeffedf3ae8 100644
--- a/nvidia_nim/tests/test_unit.py
+++ b/nvidia_nim/tests/test_unit.py
@@ -18,7 +18,7 @@ def test_check_nvidia_nim(dd_run_check, aggregator, datadog_agent, instance):
     check = NvidiaNIMCheck("nvidia_nim", {}, [instance])
     check.check_id = "test:123"
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         side_effect=[
             MockResponse(file_path=get_fixture_path("nim_metrics.txt")),
             MockResponse(file_path=get_fixture_path("nim_version.json")),
diff --git a/octopus_deploy/tests/conftest.py b/octopus_deploy/tests/conftest.py
index fee5a733376d9..7ec3897c84a13 100644
--- a/octopus_deploy/tests/conftest.py
+++ b/octopus_deploy/tests/conftest.py
@@ -214,5 +214,5 @@ def get(url, *args, **kwargs):
         return CopyingMock(elapsed=mock_elapsed, json=mock_json, status_code=mock_status_code)
 
     mock_get = CopyingMock(side_effect=get)
-    monkeypatch.setattr('requests.get', mock_get)
+    monkeypatch.setattr('requests.Session.get', mock_get)
     return mock_get
diff --git a/openstack_controller/tests/conftest.py b/openstack_controller/tests/conftest.py
index 2583431328406..e6b933bb66871 100644
--- a/openstack_controller/tests/conftest.py
+++ b/openstack_controller/tests/conftest.py
@@ -1009,7 +1009,7 @@ def get(url, *args, **kwargs):
         return mock.MagicMock(elapsed=mock_elapsed, json=mock_json, status_code=mock_status_code)
 
     mock_get = mock.MagicMock(side_effect=get)
-    monkeypatch.setattr('requests.get', mock_get)
+    monkeypatch.setattr('requests.Session.get', mock_get)
     return mock_get
 
 
@@ -1041,5 +1041,5 @@ def post(url, *args, **kwargs):
         return MockResponse(json_data=json_data, status_code=200, headers=headers)
 
     mock_post = mock.MagicMock(side_effect=post)
-    monkeypatch.setattr('requests.post', mock_post)
+    monkeypatch.setattr('requests.Session.post', mock_post)
     return mock_post
diff --git a/openstack_controller/tests/legacy/test_openstack.py b/openstack_controller/tests/legacy/test_openstack.py
index 50461fe84ef42..fe1559b5c8b0f 100644
--- a/openstack_controller/tests/legacy/test_openstack.py
+++ b/openstack_controller/tests/legacy/test_openstack.py
@@ -42,7 +42,7 @@ def test_api_error_log_no_password(check, instance, caplog):
 
     with caplog.at_level(logging.DEBUG):
         with pytest.raises(KeystoneUnreachable):
-            with mock.patch('datadog_checks.base.utils.http.requests.post') as req:
+            with mock.patch('datadog_checks.base.utils.http.requests.Session.post') as req:
                 req.side_effect = HTTPError(mock.Mock(status=404), 'not found')
                 check._api = SimpleApi(check.log, instance.get("keystone_server_url"), check.http)
                 identity = Authenticator._get_user_identity(instance.get("user"))
diff --git a/openstack_controller/tests/legacy/test_simple_api.py b/openstack_controller/tests/legacy/test_simple_api.py
index e8346cc4f44de..3e5c30486982b 100644
--- a/openstack_controller/tests/legacy/test_simple_api.py
+++ b/openstack_controller/tests/legacy/test_simple_api.py
@@ -775,7 +775,7 @@ def test__make_request_failure(requests_wrapper):
         api = ApiFactory.create(log, instance, requests_wrapper)
 
     response_mock = mock.MagicMock()
-    with mock.patch("datadog_checks.openstack_controller.legacy.api.requests.get", return_value=response_mock):
+    with mock.patch("datadog_checks.openstack_controller.legacy.api.requests.Session.get", return_value=response_mock):
         response_mock.raise_for_status.side_effect = requests.exceptions.HTTPError
         response_mock.status_code = 401
         with pytest.raises(AuthenticationNeeded):
diff --git a/php_fpm/tests/test_unit.py b/php_fpm/tests/test_unit.py
index ec4212b8e585b..b0f46d613c077 100644
--- a/php_fpm/tests/test_unit.py
+++ b/php_fpm/tests/test_unit.py
@@ -38,7 +38,8 @@ def test_should_not_retry(check, instance):
     backoff only works when response code is 503, otherwise the error
     should bubble up
     """
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.side_effect = FooException("Generic http error here")
         with pytest.raises(FooException):
             check._process_status(instance['status_url'], [], None, False)
@@ -48,7 +49,8 @@ def test_should_bail_out(check, instance):
     """
     backoff should give up after 3 attempts
     """
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         attrs = {'raise_for_status.side_effect': FooException()}
         r.get.side_effect = [
             mock.MagicMock(status_code=503, **attrs),
@@ -65,7 +67,8 @@ def test_backoff_success(check, instance, aggregator, payload):
     Success after 2 failed attempts
     """
     instance['ping_url'] = None
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         attrs = {'json.return_value': payload}
         r.get.side_effect = [
             mock.MagicMock(status_code=503),
@@ -103,7 +106,8 @@ def test_config(test_case, extra_config, expected_http_kwargs, dd_run_check):
     instance.update(extra_config)
     check = PHPFPMCheck('php_fpm', {}, instances=[instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200)
 
         dd_run_check(check)
diff --git a/powerdns_recursor/tests/test_metadata.py b/powerdns_recursor/tests/test_metadata.py
index a7f8511818c68..36ff99eebd981 100644
--- a/powerdns_recursor/tests/test_metadata.py
+++ b/powerdns_recursor/tests/test_metadata.py
@@ -24,19 +24,19 @@ def test_metadata_unit(datadog_agent):
 
     config_obj, tags = check._get_config(instance)
 
-    with mock.patch('requests.get', side_effect=requests.exceptions.Timeout()):
+    with mock.patch('requests.Session.get', side_effect=requests.exceptions.Timeout()):
         check._collect_metadata(config_obj)
         datadog_agent.assert_metadata_count(0)
         check.log.debug.assert_called_with('Error collecting PowerDNS Recursor version: %s', '')
 
     datadog_agent.reset()
-    with mock.patch('requests.get', return_value=MockResponse()):
+    with mock.patch('requests.Session.get', return_value=MockResponse()):
         check._collect_metadata(config_obj)
         datadog_agent.assert_metadata_count(0)
         check.log.debug.assert_called_with("Couldn't find the PowerDNS Recursor Server version header")
 
     datadog_agent.reset()
-    with mock.patch('requests.get', return_value=MockResponse(headers={'Server': 'wrong_stuff'})):
+    with mock.patch('requests.Session.get', return_value=MockResponse(headers={'Server': 'wrong_stuff'})):
         check._collect_metadata(config_obj)
         datadog_agent.assert_metadata_count(0)
         check.log.debug.assert_called_with(
diff --git a/prometheus/tests/conftest.py b/prometheus/tests/conftest.py
index dfffd2ff931a3..853e8f5e99efd 100644
--- a/prometheus/tests/conftest.py
+++ b/prometheus/tests/conftest.py
@@ -63,7 +63,7 @@ def poll_mock():
     g3.labels(matched_label="foobar", node="host2", timestamp="456").set(float('inf'))
 
     poll_mock_patch = mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: ensure_unicode(generate_latest(registry)).split("\n"),
diff --git a/proxysql/tests/test_unit.py b/proxysql/tests/test_unit.py
index fc292e22b0908..0c842bdb1f1a3 100644
--- a/proxysql/tests/test_unit.py
+++ b/proxysql/tests/test_unit.py
@@ -101,7 +101,7 @@ def test_config_ok(dd_run_check, instance_basic):
 
 @pytest.mark.unit
 def test_tls_config_ok(dd_run_check, instance_basic_tls):
-    with mock.patch('datadog_checks.base.utils.tls.ssl') as ssl:
+    with mock.patch('datadog_checks.base.utils.http.ssl') as ssl:
         with mock.patch('datadog_checks.proxysql.proxysql.pymysql') as pymysql:
             check = get_check(instance_basic_tls)
 
diff --git a/rabbitmq/tests/test_openmetrics.py b/rabbitmq/tests/test_openmetrics.py
index c414af567610c..6fcfea374c5c4 100644
--- a/rabbitmq/tests/test_openmetrics.py
+++ b/rabbitmq/tests/test_openmetrics.py
@@ -245,7 +245,7 @@ def test_aggregated_and_unaggregated_endpoints(endpoint, metrics, aggregator, dd
             'include_aggregated_endpoint': True,
         }
     )
-    mocker.patch('requests.get', wraps=mock_http_responses)
+    mocker.patch('requests.Session.get', wraps=mock_http_responses)
     dd_run_check(check)
 
     meta_metrics = {'rabbitmq.build_info', 'rabbitmq.identity_info'}
@@ -289,7 +289,7 @@ def test_detailed_only_metrics(aggregator, dd_run_check, mocker):
             'include_aggregated_endpoint': True,
         }
     )
-    mocker.patch('requests.get', wraps=mock_http_responses)
+    mocker.patch('requests.Session.get', wraps=mock_http_responses)
     dd_run_check(check)
 
     detailed_only_metrics = (
diff --git a/rabbitmq/tests/test_unit.py b/rabbitmq/tests/test_unit.py
index f26ae5b38ca95..9075a7526dbec 100644
--- a/rabbitmq/tests/test_unit.py
+++ b/rabbitmq/tests/test_unit.py
@@ -25,7 +25,8 @@
 
 
 def test__get_data(check):
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.side_effect = [requests.exceptions.HTTPError, ValueError]
         with pytest.raises(RabbitMQException) as e:
             check._get_data('')
@@ -138,7 +139,8 @@ def test_config(check, test_case, extra_config, expected_http_kwargs):
     config.update(extra_config)
     check = RabbitMQ('rabbitmq', {}, instances=[config])
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as r:
+    r = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=r):
         r.get.return_value = mock.MagicMock(status_code=200)
 
         check.check(config)
diff --git a/ray/tests/test_unit.py b/ray/tests/test_unit.py
index c11b8ad455759..f2e7725b5287f 100644
--- a/ray/tests/test_unit.py
+++ b/ray/tests/test_unit.py
@@ -17,7 +17,7 @@
     ],
 )
 def test_check(dd_run_check, aggregator, mocker, check, instance, metrics):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     dd_run_check(check(instance))
 
     for expected_metric in metrics:
@@ -33,7 +33,7 @@ def test_check(dd_run_check, aggregator, mocker, check, instance, metrics):
 def test_invalid_url(dd_run_check, aggregator, check, mocked_head_instance, mocker):
     mocked_head_instance["openmetrics_endpoint"] = "http://unknowwn"
 
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     with pytest.raises(Exception):
         dd_run_check(check(mocked_head_instance))
 
diff --git a/scylla/tests/conftest.py b/scylla/tests/conftest.py
index b4b653494b3ae..5b28e13609d02 100644
--- a/scylla/tests/conftest.py
+++ b/scylla/tests/conftest.py
@@ -45,7 +45,7 @@ def mock_db_data():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200,
             iter_lines=lambda **kwargs: text_data.split("\n"),
diff --git a/sonatype_nexus/tests/test_check.py b/sonatype_nexus/tests/test_check.py
index 7f6a8064ac9dd..eda941ff13609 100644
--- a/sonatype_nexus/tests/test_check.py
+++ b/sonatype_nexus/tests/test_check.py
@@ -15,7 +15,7 @@
 @pytest.fixture
 def mock_http_response(mocker):
     yield lambda *args, **kwargs: mocker.patch(
-        kwargs.pop("method", "requests.get"), return_value=MockResponse(*args, **kwargs)
+        kwargs.pop("method", "requests.Session.get"), return_value=MockResponse(*args, **kwargs)
     )
 
 
diff --git a/spark/datadog_checks/spark/spark.py b/spark/datadog_checks/spark/spark.py
index d23d5815863a7..c0c74979f8f0d 100644
--- a/spark/datadog_checks/spark/spark.py
+++ b/spark/datadog_checks/spark/spark.py
@@ -51,6 +51,7 @@ class SparkCheck(AgentCheck):
     HTTP_CONFIG_REMAPPER = {
         'ssl_verify': {'name': 'tls_verify'},
         'ssl_cert': {'name': 'tls_cert'},
+        'ssl_ca_cert': {'name': 'tls_ca_cert'},
         'ssl_key': {'name': 'tls_private_key'},
     }
 
diff --git a/spark/tests/test_spark.py b/spark/tests/test_spark.py
index 364cd15a3949b..4cdab4c4201f0 100644
--- a/spark/tests/test_spark.py
+++ b/spark/tests/test_spark.py
@@ -178,7 +178,7 @@ def get_default_mock(url):
     raise KeyError(f"{url} does not match any response fixtures.")
 
 
-def yarn_requests_get_mock(url, *args, **kwargs):
+def yarn_requests_get_mock(session, url, *args, **kwargs):
     arg_url = Url(url)
 
     if arg_url == YARN_APP_URL:
@@ -188,7 +188,7 @@ def yarn_requests_get_mock(url, *args, **kwargs):
     return get_default_mock(url)
 
 
-def yarn_requests_auth_mock(*args, **kwargs):
+def yarn_requests_auth_mock(session, url, *args, **kwargs):
     # Make sure we're passing in authentication
     assert 'auth' in kwargs, "Error, missing authentication"
 
@@ -196,10 +196,10 @@ def yarn_requests_auth_mock(*args, **kwargs):
     assert kwargs['auth'] == (TEST_USERNAME, TEST_PASSWORD), "Incorrect username or password"
 
     # Return mocked request.get(...)
-    return yarn_requests_get_mock(*args, **kwargs)
+    return yarn_requests_get_mock(session, url, *args, **kwargs)
 
 
-def mesos_requests_get_mock(url, *args, **kwargs):
+def mesos_requests_get_mock(session, url, *args, **kwargs):
     arg_url = Url(url)
 
     if arg_url == MESOS_APP_URL:
@@ -220,7 +220,7 @@ def mesos_requests_get_mock(url, *args, **kwargs):
         return MockResponse(file_path=os.path.join(FIXTURE_DIR, 'metrics_json'))
 
 
-def driver_requests_get_mock(url, *args, **kwargs):
+def driver_requests_get_mock(session, url, *args, **kwargs):
     arg_url = Url(url)
 
     if arg_url == DRIVER_APP_URL:
@@ -241,7 +241,7 @@ def driver_requests_get_mock(url, *args, **kwargs):
         return MockResponse(file_path=os.path.join(FIXTURE_DIR, 'metrics_json'))
 
 
-def standalone_requests_get_mock(url, *args, **kwargs):
+def standalone_requests_get_mock(session, url, *args, **kwargs):
     arg_url = Url(url)
 
     if arg_url == STANDALONE_APP_URL:
@@ -264,7 +264,7 @@ def standalone_requests_get_mock(url, *args, **kwargs):
         return MockResponse(file_path=os.path.join(FIXTURE_DIR, 'metrics_json'))
 
 
-def standalone_requests_pre20_get_mock(url, *args, **kwargs):
+def standalone_requests_pre20_get_mock(session, url, *args, **kwargs):
     arg_url = Url(url)
 
     if arg_url == STANDALONE_APP_URL:
@@ -299,7 +299,7 @@ def standalone_requests_pre20_get_mock(url, *args, **kwargs):
         return MockResponse(file_path=os.path.join(FIXTURE_DIR, 'metrics_json'))
 
 
-def proxy_with_warning_page_mock(url, *args, **kwargs):
+def proxy_with_warning_page_mock(session, url, *args, **kwargs):
     cookies = kwargs.get('cookies') or {}
     proxy_cookie = cookies.get('proxy_cookie')
     url_parts = list(urlparse(url))
@@ -307,7 +307,7 @@ def proxy_with_warning_page_mock(url, *args, **kwargs):
     if proxy_cookie and query.get('proxyapproved') == 'true':
         del query['proxyapproved']
         url_parts[4] = urlencode(query)
-        return standalone_requests_get_mock(urlunparse(url_parts), *args[1:], **kwargs)
+        return standalone_requests_get_mock(session, urlunparse(url_parts), *args[1:], **kwargs)
     else:
         # Display the html warning page with the redirect link
         query['proxyapproved'] = 'true'
@@ -404,7 +404,8 @@ def proxy_with_warning_page_mock(url, *args, **kwargs):
     'spark_url': SSL_SERVER_URL,
     'cluster_name': CLUSTER_NAME,
     'spark_cluster_mode': 'spark_standalone_mode',
-    'ssl_verify': os.path.join(CERTIFICATE_DIR, 'cert.cert'),
+    'ssl_verify': True,
+    'ssl_ca_cert': os.path.join(CERTIFICATE_DIR, 'cert.cert'),
     'executor_level_metrics': True,
 }
 
@@ -688,7 +689,7 @@ def _assert(aggregator, values_and_tags):
 
 @pytest.mark.unit
 def test_yarn(aggregator, dd_run_check):
-    with mock.patch('requests.get', yarn_requests_get_mock):
+    with mock.patch('requests.Session.get', yarn_requests_get_mock):
         c = SparkCheck('spark', {}, [YARN_CONFIG])
         dd_run_check(c)
 
@@ -743,7 +744,7 @@ def test_yarn(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_auth_yarn(aggregator, dd_run_check):
-    with mock.patch('requests.get', yarn_requests_auth_mock):
+    with mock.patch('requests.Session.get', yarn_requests_auth_mock):
         c = SparkCheck('spark', {}, [YARN_AUTH_CONFIG])
         dd_run_check(c)
 
@@ -763,7 +764,7 @@ def test_auth_yarn(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_mesos(aggregator, dd_run_check):
-    with mock.patch('requests.get', mesos_requests_get_mock):
+    with mock.patch('requests.Session.get', mesos_requests_get_mock):
         c = SparkCheck('spark', {}, [MESOS_CONFIG])
         dd_run_check(c)
         _assert(
@@ -822,7 +823,7 @@ def test_mesos(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_mesos_filter(aggregator, dd_run_check):
-    with mock.patch('requests.get', mesos_requests_get_mock):
+    with mock.patch('requests.Session.get', mesos_requests_get_mock):
         c = SparkCheck('spark', {}, [MESOS_FILTERED_CONFIG])
         dd_run_check(c)
 
@@ -835,7 +836,7 @@ def test_mesos_filter(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_driver_unit(aggregator, dd_run_check):
-    with mock.patch('requests.get', driver_requests_get_mock):
+    with mock.patch('requests.Session.get', driver_requests_get_mock):
         c = SparkCheck('spark', {}, [DRIVER_CONFIG])
         dd_run_check(c)
 
@@ -895,7 +896,7 @@ def test_driver_unit(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_standalone_unit(aggregator, dd_run_check):
-    with mock.patch('requests.get', standalone_requests_get_mock):
+    with mock.patch('requests.Session.get', standalone_requests_get_mock):
         c = SparkCheck('spark', {}, [STANDALONE_CONFIG])
         dd_run_check(c)
 
@@ -947,7 +948,7 @@ def test_standalone_unit(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_standalone_stage_disabled_unit(aggregator, dd_run_check):
-    with mock.patch('requests.get', standalone_requests_get_mock):
+    with mock.patch('requests.Session.get', standalone_requests_get_mock):
         c = SparkCheck('spark', {}, [STANDALONE_CONFIG_STAGE_DISABLED])
         dd_run_check(c)
 
@@ -996,7 +997,7 @@ def test_standalone_stage_disabled_unit(aggregator, dd_run_check):
 @pytest.mark.unit
 def test_standalone_unit_with_proxy_warning_page(aggregator, dd_run_check):
     c = SparkCheck('spark', {}, [STANDALONE_CONFIG])
-    with mock.patch('requests.get', proxy_with_warning_page_mock):
+    with mock.patch('requests.Session.get', proxy_with_warning_page_mock):
         dd_run_check(c)
 
         _assert(
@@ -1048,7 +1049,7 @@ def test_standalone_unit_with_proxy_warning_page(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_standalone_pre20(aggregator, dd_run_check):
-    with mock.patch('requests.get', standalone_requests_pre20_get_mock):
+    with mock.patch('requests.Session.get', standalone_requests_pre20_get_mock):
         c = SparkCheck('spark', {}, [STANDALONE_CONFIG_PRE_20])
         dd_run_check(c)
 
@@ -1101,7 +1102,7 @@ def test_standalone_pre20(aggregator, dd_run_check):
 
 @pytest.mark.unit
 def test_metadata(aggregator, datadog_agent, dd_run_check):
-    with mock.patch('requests.get', standalone_requests_pre20_get_mock):
+    with mock.patch('requests.Session.get', standalone_requests_pre20_get_mock):
         c = SparkCheck(CHECK_NAME, {}, [STANDALONE_CONFIG_PRE_20])
         c.check_id = "test:123"
         dd_run_check(c)
@@ -1127,7 +1128,7 @@ def test_disable_legacy_cluster_tags(aggregator, dd_run_check):
     instance = MESOS_FILTERED_CONFIG
     instance['disable_legacy_cluster_tag'] = True
 
-    with mock.patch('requests.get', mesos_requests_get_mock):
+    with mock.patch('requests.Session.get', mesos_requests_get_mock):
         c = SparkCheck('spark', {}, [instance])
         dd_run_check(c)
 
@@ -1156,7 +1157,7 @@ def test_enable_query_name_tag_for_structured_streaming(
 ):
     instance['enable_query_name_tag'] = True
 
-    with mock.patch('requests.get', requests_get_mock):
+    with mock.patch('requests.Session.get', requests_get_mock):
         c = SparkCheck('spark', {}, [instance])
         dd_run_check(c)
 
@@ -1240,7 +1241,7 @@ def test_do_not_crash_on_single_app_failure():
     ids=["driver", "yarn", "mesos", "standalone", "standalone_pre_20"],
 )
 def test_no_running_apps(aggregator, dd_run_check, instance, service_check, caplog):
-    with mock.patch('requests.get', return_value=MockResponse("{}")):
+    with mock.patch('requests.Session.get', return_value=MockResponse("{}")):
         with caplog.at_level(logging.WARNING):
             dd_run_check(SparkCheck('spark', {}, [instance]))
 
@@ -1288,7 +1289,7 @@ def test_yarn_no_json_for_app_properties(
     In these cases we skip only the specific missing apps and metrics while collecting all others.
     """
 
-    def get_without_json(url, *args, **kwargs):
+    def get_without_json(session, url, *args, **kwargs):
         arg_url = Url(url)
         if arg_url == property_url:
             return mock_response
@@ -1322,9 +1323,9 @@ def get_without_json(url, *args, **kwargs):
                 ]
             )
         else:
-            return yarn_requests_get_mock(url, *args, **kwargs)
+            return yarn_requests_get_mock(session, url, *args, **kwargs)
 
-    mocker.patch('requests.get', get_without_json)
+    mocker.patch('requests.Session.get', get_without_json)
     dd_run_check(SparkCheck('spark', {}, [YARN_CONFIG]))
     for m in missing_metrics:
         aggregator.assert_metric_has_tag(m, 'app_name:PySparkShell', count=0)
diff --git a/squid/tests/test_squid.py b/squid/tests/test_squid.py
index 9732198af7bf9..55a40cbe7c835 100644
--- a/squid/tests/test_squid.py
+++ b/squid/tests/test_squid.py
@@ -79,7 +79,7 @@ def test_check_ok(aggregator, check, instance):
 )
 @pytest.mark.usefixtures("dd_environment")
 def test_version_metadata(check, instance, datadog_agent, raw_version, version_metadata, count):
-    with mock.patch('datadog_checks.base.utils.http.requests.get') as g:
+    with mock.patch('datadog_checks.base.utils.http.requests.Session.get') as g:
         g.return_value.headers = {'Server': raw_version}
 
         check.check_id = 'test:123'
diff --git a/squid/tests/test_unit.py b/squid/tests/test_unit.py
index b6bffb0936202..332e8c9123e2d 100644
--- a/squid/tests/test_unit.py
+++ b/squid/tests/test_unit.py
@@ -62,7 +62,7 @@ def test_get_counters(check):
     due to a missing = character.
     See https://github.com/DataDog/integrations-core/pull/1643
     """
-    with mock.patch('datadog_checks.squid.squid.requests.get') as g:
+    with mock.patch('datadog_checks.squid.squid.requests.Session.get') as g:
         with mock.patch('datadog_checks.squid.SquidCheck.submit_version'):
             g.return_value = mock.MagicMock(text="client_http.requests=42\n\n")
             check.parse_counter = mock.MagicMock(return_value=('foo', 'bar'))
@@ -73,7 +73,7 @@ def test_get_counters(check):
 
 
 def test_host_without_protocol(check, instance):
-    with mock.patch('datadog_checks.squid.squid.requests.get') as g:
+    with mock.patch('datadog_checks.squid.squid.requests.Session.get') as g:
         with mock.patch('datadog_checks.squid.SquidCheck.submit_version'):
             g.return_value = mock.MagicMock(text="client_http.requests=42\n\n")
             check.parse_counter = mock.MagicMock(return_value=('foo', 'bar'))
@@ -83,7 +83,7 @@ def test_host_without_protocol(check, instance):
 
 def test_host_https(check, instance):
     instance['host'] = 'https://localhost'
-    with mock.patch('datadog_checks.squid.squid.requests.get') as g:
+    with mock.patch('datadog_checks.squid.squid.requests.Session.get') as g:
         with mock.patch('datadog_checks.squid.SquidCheck.submit_version'):
             g.return_value = mock.MagicMock(text="client_http.requests=42\n\n")
             check.parse_counter = mock.MagicMock(return_value=('foo', 'bar'))
@@ -103,7 +103,7 @@ def test_legacy_username_password(instance, auth_config):
     instance.update(auth_config)
     check = SquidCheck(common.CHECK_NAME, {}, {}, [instance])
 
-    with mock.patch('datadog_checks.base.utils.http.requests.get') as g:
+    with mock.patch('datadog_checks.base.utils.http.requests.Session.get') as g:
         with mock.patch('datadog_checks.squid.SquidCheck.submit_version'):
             check.get_counters('host', 'port', [])
 
diff --git a/strimzi/tests/test_unit.py b/strimzi/tests/test_unit.py
index 71da37cde60ab..0c9475cefab1a 100644
--- a/strimzi/tests/test_unit.py
+++ b/strimzi/tests/test_unit.py
@@ -56,7 +56,7 @@ def test_check_unique_operator(
     tag,
     mocker,
 ):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     dd_run_check(check(instance))
 
     for expected_metric in metrics:
@@ -76,7 +76,7 @@ def test_check_unique_operator(
 
 
 def test_check_all_operators(dd_run_check, aggregator, check, mocker):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     dd_run_check(
         check(
             {
diff --git a/teamcity/tests/test_teamcity.py b/teamcity/tests/test_teamcity.py
index caa815916ae1c..65c23a4a12dab 100644
--- a/teamcity/tests/test_teamcity.py
+++ b/teamcity/tests/test_teamcity.py
@@ -66,7 +66,7 @@ def test_config(dd_run_check, extra_config, expected_http_kwargs):
     instance.update(extra_config)
     check = TeamCityRest('teamcity', {}, [instance])
 
-    with patch('datadog_checks.base.utils.http.requests.get') as r:
+    with patch('datadog_checks.base.utils.http.requests.Session.get') as r:
         dd_run_check(check)
 
         http_wargs = {
diff --git a/tekton/tests/test_unit.py b/tekton/tests/test_unit.py
index 83bd63353b527..0010a2eae466d 100644
--- a/tekton/tests/test_unit.py
+++ b/tekton/tests/test_unit.py
@@ -17,7 +17,7 @@
     ],
 )
 def test_check(dd_run_check, aggregator, mocker, instance, metrics, request, namespace):
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     dd_run_check(check(request.getfixturevalue(instance)))
 
     for expected_metric in metrics:
@@ -33,7 +33,7 @@ def test_check(dd_run_check, aggregator, mocker, instance, metrics, request, nam
 def test_invalid_url(dd_run_check, aggregator, pipelines_instance, mocker):
     pipelines_instance["pipelines_controller_endpoint"] = "http://unknowwn"
 
-    mocker.patch("requests.get", wraps=mock_http_responses)
+    mocker.patch("requests.Session.get", wraps=mock_http_responses)
     with pytest.raises(Exception):
         dd_run_check(check(pipelines_instance))
 
diff --git a/temporal/tests/conftest.py b/temporal/tests/conftest.py
index c31e432914f2e..2ed04281aa8c5 100644
--- a/temporal/tests/conftest.py
+++ b/temporal/tests/conftest.py
@@ -87,7 +87,7 @@ def mock_metrics():
     with open(f_name, 'r') as f:
         text_data = f.read()
     with mock.patch(
-        'requests.get',
+        'requests.Session.get',
         return_value=mock.MagicMock(
             status_code=200, iter_lines=lambda **kwargs: text_data.split("\n"), headers={'Content-Type': "text/plain"}
         ),
diff --git a/tls/datadog_checks/tls/tls_remote.py b/tls/datadog_checks/tls/tls_remote.py
index 516b3a98b4cf1..b15db76eca847 100644
--- a/tls/datadog_checks/tls/tls_remote.py
+++ b/tls/datadog_checks/tls/tls_remote.py
@@ -179,8 +179,16 @@ def fetch_intermediate_certs(self):
 
         with sock:
             try:
-                context = ssl.SSLContext(protocol=ssl.PROTOCOL_TLS)
+                context = ssl.SSLContext(protocol=ssl.PROTOCOL_TLS_CLIENT)
                 context.verify_mode = ssl.CERT_NONE
+                ciphers = self.agent_check.tls_context_wrapper.config.get('tls_ciphers')
+                if ciphers:
+                    if 'ALL' in ciphers:
+                        updated_ciphers = "ALL"
+                    else:
+                        updated_ciphers = ":".join(ciphers)
+
+                    context.set_ciphers(updated_ciphers)
 
                 with context.wrap_socket(sock, server_hostname=self.agent_check._server_hostname) as secure_sock:
                     der_cert = secure_sock.getpeercert(binary_form=True)
diff --git a/torchserve/tests/inference/test_unit.py b/torchserve/tests/inference/test_unit.py
index 9cae5f90b3c8e..a965bd8b23fce 100644
--- a/torchserve/tests/inference/test_unit.py
+++ b/torchserve/tests/inference/test_unit.py
@@ -13,7 +13,7 @@
 
 
 def test_check(dd_run_check, aggregator, check, mocked_inference_instance, mocker):
-    mocker.patch('requests.get', wraps=mock_http_responses())
+    mocker.patch('requests.Session.get', wraps=mock_http_responses())
     dd_run_check(check(mocked_inference_instance))
 
     aggregator.assert_service_check(
diff --git a/torchserve/tests/management/test_model_discovery.py b/torchserve/tests/management/test_model_discovery.py
index de5f97c04fc23..ea17df181c441 100644
--- a/torchserve/tests/management/test_model_discovery.py
+++ b/torchserve/tests/management/test_model_discovery.py
@@ -109,7 +109,8 @@ def test_get_models(check, mocked_management_instance, expected_models, fixture_
                 mock_resp.raise_for_status.side_effect = HTTPError() if status_code != 200 else None
                 responses.append(mock_resp)
 
-    with mock.patch('datadog_checks.base.utils.http.requests') as req:
+    req = mock.MagicMock()
+    with mock.patch('datadog_checks.base.utils.http.requests.Session', return_value=req):
         discovery = ModelDiscovery(check(mocked_management_instance), include=[".*"])
         req.get.side_effect = responses
         assert [('.*', model['modelName'], model, None) for model in expected_models] == list(discovery.get_items())
diff --git a/torchserve/tests/management/test_unit.py b/torchserve/tests/management/test_unit.py
index 7a2f7705ba133..15cd3b694faff 100644
--- a/torchserve/tests/management/test_unit.py
+++ b/torchserve/tests/management/test_unit.py
@@ -14,7 +14,7 @@
 
 
 def test_check(dd_run_check, aggregator, check, mocked_management_instance, mocker):
-    mocker.patch('requests.get', wraps=mock_http_responses())
+    mocker.patch('requests.Session.get', wraps=mock_http_responses())
     dd_run_check(check(mocked_management_instance))
 
     for metric in METRICS:
@@ -43,7 +43,7 @@ def custom_mock_http_responses(url, **_params):
 
         return mock_http_responses()(url)
 
-    mocker.patch('requests.get', wraps=custom_mock_http_responses)
+    mocker.patch('requests.Session.get', wraps=custom_mock_http_responses)
     dd_run_check(check(mocked_management_instance))
 
     # We should not get anything for these models
@@ -157,7 +157,7 @@ def custom_mock_http_responses(url, **_params):
 def test_check_with_discovery(
     dd_run_check, aggregator, check, mocked_management_instance, mocker, include, exclude, limit, expected_models
 ):
-    mocker.patch('requests.get', wraps=mock_http_responses())
+    mocker.patch('requests.Session.get', wraps=mock_http_responses())
     mocked_management_instance["limit"] = limit
     mocked_management_instance["exclude"] = exclude
     mocked_management_instance["include"] = include
@@ -308,13 +308,13 @@ def test_check_with_events(
     datadog_agent.reset()
 
     check_instance = check(mocked_management_instance)
-    mocker.patch('requests.get', wraps=mock_http_responses())
+    mocker.patch('requests.Session.get', wraps=mock_http_responses())
     dd_run_check(check_instance)
     dd_run_check(check_instance)
 
     assert len(aggregator.events) == 0
 
-    mocker.patch('requests.get', wraps=mock_http_responses(new_response))
+    mocker.patch('requests.Session.get', wraps=mock_http_responses(new_response))
     dd_run_check(check_instance)
 
     for expected_event, actual_event in zip(expected_events, aggregator.events, strict=True):
@@ -338,13 +338,13 @@ def test_check_disable_events(dd_run_check, datadog_agent, aggregator, check, mo
     mocked_management_instance["submit_events"] = False
 
     check_instance = check(mocked_management_instance)
-    mocker.patch('requests.get', wraps=mock_http_responses())
+    mocker.patch('requests.Session.get', wraps=mock_http_responses())
     dd_run_check(check_instance)
     dd_run_check(check_instance)
 
     assert len(aggregator.events) == 0
 
-    mocker.patch('requests.get', wraps=mock_http_responses("management/events/models_all_dropped.json"))
+    mocker.patch('requests.Session.get', wraps=mock_http_responses("management/events/models_all_dropped.json"))
     dd_run_check(check_instance)
 
     assert len(aggregator.events) == 0
diff --git a/torchserve/tests/openmetrics/test_unit.py b/torchserve/tests/openmetrics/test_unit.py
index 5964f02bcae23..78693ed4ab288 100644
--- a/torchserve/tests/openmetrics/test_unit.py
+++ b/torchserve/tests/openmetrics/test_unit.py
@@ -13,7 +13,7 @@
 
 
 def test_check(dd_run_check, aggregator, check, mocked_openmetrics_instance, mocker):
-    mocker.patch('requests.get', wraps=mock_http_responses())
+    mocker.patch('requests.Session.get', wraps=mock_http_responses())
     dd_run_check(check(mocked_openmetrics_instance))
 
     for name, expected_values in METRICS.items():
diff --git a/twistlock/tests/test_twistlock.py b/twistlock/tests/test_twistlock.py
index b832e4f3f3fdb..aaba9d57bf62d 100644
--- a/twistlock/tests/test_twistlock.py
+++ b/twistlock/tests/test_twistlock.py
@@ -35,7 +35,7 @@
 
 
 def mock_get_factory(fixture_group):
-    def mock_get(url, *args, **kwargs):
+    def mock_get(session, url, *args, **kwargs):
         split_url = url.split('/')
         path = split_url[-1]
         return MockResponse(file_path=os.path.join(HERE, 'fixtures', fixture_group, '{}.json'.format(path)))
@@ -48,7 +48,7 @@ def test_check(aggregator, instance, fixture_group):
 
     check = TwistlockCheck('twistlock', {}, [instance])
 
-    with mock.patch('requests.get', side_effect=mock_get_factory(fixture_group), autospec=True):
+    with mock.patch('requests.Session.get', side_effect=mock_get_factory(fixture_group), autospec=True):
         check.check(instance)
         check.check(instance)
 
@@ -70,11 +70,12 @@ def test_config_project(aggregator, instance, fixture_group):
     instance['project'] = project
     check = TwistlockCheck('twistlock', {}, [instance])
 
-    with mock.patch('requests.get', side_effect=mock_get_factory(fixture_group), autospec=True) as r:
+    with mock.patch('requests.Session.get', side_effect=mock_get_factory(fixture_group), autospec=True) as r:
         check.check(instance)
 
         r.assert_called_with(
-            mock.ANY,
+            mock.ANY,  # The session object is passed as the first argument
+            mock.ANY,  # The URL is passed as the second argument
             params=qparams,
             auth=mock.ANY,
             cert=mock.ANY,
@@ -101,7 +102,7 @@ def mock_get(url, *args, **kwargs):
             return MockResponse(file_path=os.path.join(HERE, 'fixtures', fixture_group, '{}.json'.format(path)))
         return MockResponse(file_path=os.path.join(HERE, 'fixtures', 'empty_images.json'))
 
-    with mock.patch('requests.get', side_effect=mock_get):
+    with mock.patch('requests.Session.get', side_effect=mock_get):
         check.check(instance)
         check.check(instance)
 
@@ -111,7 +112,9 @@ def test_err_response(aggregator, instance):
     check = TwistlockCheck('twistlock', {}, [instance])
 
     with pytest.raises(Exception, match='^Error in response'):
-        with mock.patch('requests.get', return_value=MockResponse('{"err": "invalid credentials"}'), autospec=True):
+        with mock.patch(
+            'requests.Session.get', return_value=MockResponse('{"err": "invalid credentials"}'), autospec=True
+        ):
 
             check.check(instance)
 
diff --git a/vault/tests/test_vault.py b/vault/tests/test_vault.py
index 81c37dceff840..12691eedfc1d7 100644
--- a/vault/tests/test_vault.py
+++ b/vault/tests/test_vault.py
@@ -76,7 +76,7 @@ def test_service_check_connect_ok_all_tags(self, aggregator, dd_run_check, globa
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={'ha_enabled': False, 'is_self': True, 'leader_address': '', 'leader_cluster_address': ''}
@@ -97,7 +97,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         aggregator.assert_service_check(Vault.SERVICE_CHECK_CONNECT, status=Vault.OK, tags=global_tags, count=1)
@@ -135,7 +135,7 @@ def test_service_check_500_fail(self, aggregator, dd_run_check, global_tags):
         instance.update(INSTANCES['main'])
         c = Vault(Vault.CHECK_NAME, {}, [instance])
 
-        with mock.patch('requests.get', return_value=MockResponse(status_code=500)):
+        with mock.patch('requests.Session.get', return_value=MockResponse(status_code=500)):
             with pytest.raises(
                 Exception, match=r'^The Vault endpoint `{}.+?` returned 500$'.format(re.escape(instance['api_url']))
             ):
@@ -169,7 +169,7 @@ def test_service_check_unsealed_ok_all_tags(self, aggregator, dd_run_check, glob
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={'ha_enabled': False, 'is_self': True, 'leader_address': '', 'leader_cluster_address': ''}
@@ -190,7 +190,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         expected_tags = [
@@ -212,7 +212,7 @@ def test_service_check_unsealed_fail(self, aggregator, dd_run_check, use_openmet
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/health':
                 return MockResponse(
                     json_data={
@@ -230,7 +230,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         aggregator.assert_service_check(Vault.SERVICE_CHECK_UNSEALED, status=Vault.CRITICAL, count=1)
@@ -253,7 +253,7 @@ def test_service_check_initialized_ok_all_tags(self, aggregator, dd_run_check, g
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={'ha_enabled': False, 'is_self': True, 'leader_address': '', 'leader_cluster_address': ''}
@@ -274,7 +274,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         expected_tags = [
@@ -296,7 +296,7 @@ def test_service_check_initialized_fail(self, aggregator, dd_run_check, use_open
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/health':
                 return MockResponse(
                     json_data={
@@ -314,7 +314,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         aggregator.assert_service_check(Vault.SERVICE_CHECK_INITIALIZED, status=Vault.CRITICAL, count=1)
@@ -327,7 +327,7 @@ def test_disable_legacy_cluster_tag(self, aggregator, dd_run_check, global_tags)
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={'ha_enabled': False, 'is_self': True, 'leader_address': '', 'leader_cluster_address': ''}
@@ -348,7 +348,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         expected_tags = [
@@ -368,7 +368,7 @@ def test_replication_dr_mode(self, aggregator, dd_run_check, use_openmetrics):
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/health':
                 return MockResponse(
                     json_data={
@@ -387,7 +387,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
             c.log.debug.assert_called_with(
                 "Detected vault in replication DR secondary mode, skipping Prometheus metric collection."
@@ -405,7 +405,7 @@ def test_replication_dr_mode_collect_secondary(self, aggregator, dd_run_check, u
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/health':
                 return MockResponse(
                     json_data={
@@ -426,7 +426,7 @@ def mock_requests_get(url, *args, **kwargs):
 
         metric_collection = 'OpenMetrics' if use_openmetrics else 'Prometheus'
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
             c.log.debug.assert_called_with(
                 "Detected vault in replication DR secondary mode but also detected that "
@@ -445,7 +445,7 @@ def test_replication_dr_mode_changed(self, aggregator, dd_run_check, use_openmet
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/health':
                 if getattr(mock_requests_get, 'first_health_call', True):
                     mock_requests_get.first_health_call = False
@@ -470,7 +470,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
             assert not c._skip_dr_metric_collection
             aggregator.assert_service_check(Vault.SERVICE_CHECK_CONNECT, status=Vault.OK, count=1)
@@ -504,7 +504,7 @@ def test_event_leader_change(self, aggregator, dd_run_check, cluster, use_openme
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={
@@ -516,7 +516,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         assert len(aggregator.events) > 0
@@ -545,7 +545,7 @@ def test_leader_change_not_self(self, aggregator, dd_run_check, use_openmetrics)
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={
@@ -557,7 +557,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         assert len(aggregator.events) == 0
@@ -571,7 +571,7 @@ def test_is_leader_metric_true(self, aggregator, dd_run_check, use_openmetrics):
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={
@@ -583,7 +583,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         aggregator.assert_metric('vault.is_leader', 1)
@@ -597,7 +597,7 @@ def test_is_leader_metric_false(self, aggregator, dd_run_check, use_openmetrics)
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(
                     json_data={
@@ -609,7 +609,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         aggregator.assert_metric('vault.is_leader', 0)
@@ -624,7 +624,7 @@ def test_sys_health_non_standard_status_codes(self, aggregator, dd_run_check, st
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/health':
                 return MockResponse(
                     json_data={
@@ -643,7 +643,7 @@ def mock_requests_get(url, *args, **kwargs):
                 )
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         aggregator.assert_metric('vault.is_leader', 1)
@@ -658,12 +658,12 @@ def test_sys_leader_non_standard_status_codes(self, aggregator, dd_run_check, us
         # Keep a reference for use during mock
         requests_get = requests.get
 
-        def mock_requests_get(url, *args, **kwargs):
+        def mock_requests_get(session, url, *args, **kwargs):
             if url == instance['api_url'] + '/sys/leader':
                 return MockResponse(json_data={'errors': ["Vault is sealed"]}, status_code=503)
             return requests_get(url, *args, **kwargs)
 
-        with mock.patch('requests.get', side_effect=mock_requests_get, autospec=True):
+        with mock.patch('requests.Session.get', side_effect=mock_requests_get, autospec=True):
             dd_run_check(c)
 
         aggregator.assert_metric('vault.is_leader', count=0)
@@ -807,9 +807,9 @@ def test_x_vault_request_header_is_set(monkeypatch, instance, dd_run_check, use_
 
     c = Vault(Vault.CHECK_NAME, {}, [instance])
 
-    requests_get = requests.get
+    requests_get = requests.Session.get
     mock_get = mock.Mock(side_effect=requests_get)
-    monkeypatch.setattr(requests, 'get', mock_get)
+    monkeypatch.setattr(requests.Session, 'get', mock_get)
 
     dd_run_check(c)
 
diff --git a/vertica/tests/test_unit.py b/vertica/tests/test_unit.py
index 09ecd3baeff81..34068a2f6cd0f 100644
--- a/vertica/tests/test_unit.py
+++ b/vertica/tests/test_unit.py
@@ -19,7 +19,7 @@
 
 def test_ssl_config_ok(aggregator, tls_instance):
     with mock.patch('datadog_checks.vertica.vertica.vertica') as vertica:
-        with mock.patch('datadog_checks.base.utils.tls.ssl') as ssl:
+        with mock.patch('datadog_checks.base.utils.http.ssl') as ssl:
             vertica.connect.return_value = mock.MagicMock()
             tls_context = mock.MagicMock()
             ssl.SSLContext.return_value = tls_context
@@ -37,7 +37,7 @@ def test_ssl_config_ok(aggregator, tls_instance):
 
 def test_ssl_legacy_config_ok(aggregator, tls_instance_legacy):
     with mock.patch('datadog_checks.vertica.vertica.vertica') as vertica:
-        with mock.patch('datadog_checks.base.utils.tls.ssl') as ssl:
+        with mock.patch('datadog_checks.base.utils.http.ssl') as ssl:
             vertica.connect.return_value = mock.MagicMock()
             tls_context = mock.MagicMock()
             ssl.SSLContext.return_value = tls_context
diff --git a/vllm/tests/test_unit.py b/vllm/tests/test_unit.py
index a7b4cc136cb6b..f6aa9f5cca85f 100644
--- a/vllm/tests/test_unit.py
+++ b/vllm/tests/test_unit.py
@@ -23,7 +23,7 @@ def test_check_vllm(dd_run_check, aggregator, datadog_agent, instance):
         MockResponse(file_path=get_fixture_path("vllm_version.json")),
     ]
 
-    with mock.patch('requests.get', side_effect=mock_responses):
+    with mock.patch('requests.Session.get', side_effect=mock_responses):
         dd_run_check(check)
 
     for metric in METRICS_MOCK:
@@ -47,7 +47,7 @@ def test_check_vllm_w_ray_prefix(dd_run_check, aggregator, datadog_agent, ray_in
         MockResponse(file_path=get_fixture_path("vllm_version.json")),
     ]
 
-    with mock.patch('requests.get', side_effect=mock_responses):
+    with mock.patch('requests.Session.get', side_effect=mock_responses):
         dd_run_check(check)
 
     for metric in METRICS_MOCK:
@@ -81,7 +81,7 @@ def test_emits_critical_openemtrics_service_check_when_service_is_down(
     """
     mock_http_response(status_code=404)
     check = vLLMCheck("vllm", {}, [instance])
-    with pytest.raises(Exception, match="requests.exceptions.HTTPError"):
+    with pytest.raises(Exception, match='requests.exceptions.HTTPError'):
         dd_run_check(check)
 
     aggregator.assert_all_metrics_covered()
diff --git a/voltdb/tests/test_integration.py b/voltdb/tests/test_integration.py
index 3aff8ab036f10..985094e4e4a59 100644
--- a/voltdb/tests/test_integration.py
+++ b/voltdb/tests/test_integration.py
@@ -74,7 +74,7 @@ def test_http_error(self, aggregator, instance):
         # type: (AggregatorStub, Instance) -> None
         check = VoltDBCheck('voltdb', {}, [instance])
 
-        with mock.patch('requests.get', side_effect=requests.RequestException('Something failed')):
+        with mock.patch('requests.Session.get', side_effect=requests.RequestException('Something failed')):
             error = check.run()
 
         assert 'Something failed' in error
@@ -88,7 +88,7 @@ def test_http_response_error(self, aggregator, instance):
 
         resp = requests.Response()
         resp.status_code = 503
-        with mock.patch('requests.get', return_value=resp):
+        with mock.patch('requests.Session.get', return_value=resp):
             error = check.run()
 
         assert '503 Server Error' in error
diff --git a/vsphere/tests/conftest.py b/vsphere/tests/conftest.py
index 91966233e1218..cf7338574e981 100644
--- a/vsphere/tests/conftest.py
+++ b/vsphere/tests/conftest.py
@@ -247,8 +247,8 @@ def mock_http_api(monkeypatch):
         http = MockHttpV7()
     else:
         http = MockHttpV6()
-    monkeypatch.setattr('requests.get', MagicMock(side_effect=http.get))
-    monkeypatch.setattr('requests.post', MagicMock(side_effect=http.post))
+    monkeypatch.setattr('requests.Session.get', MagicMock(side_effect=http.get))
+    monkeypatch.setattr('requests.Session.post', MagicMock(side_effect=http.post))
     yield http
 
 
diff --git a/vsphere/tests/test_check.py b/vsphere/tests/test_check.py
index 090e266e0ed3f..093703ca9bc57 100644
--- a/vsphere/tests/test_check.py
+++ b/vsphere/tests/test_check.py
@@ -283,7 +283,7 @@ def test_continue_if_tag_collection_fail(aggregator, dd_run_check, realtime_inst
     check = VSphereCheck('vsphere', {}, [realtime_instance])
     check.log = MagicMock()
 
-    with mock.patch('requests.post', side_effect=Exception, autospec=True):
+    with mock.patch('requests.Session.post', side_effect=Exception, autospec=True):
         dd_run_check(check)
 
     aggregator.assert_metric('vsphere.cpu.usage.avg', tags=['vcenter_server:FAKE'], hostname='10.0.0.104')
diff --git a/yarn/tests/conftest.py b/yarn/tests/conftest.py
index ac6efe6588ee8..16e5a8c5938c0 100644
--- a/yarn/tests/conftest.py
+++ b/yarn/tests/conftest.py
@@ -58,47 +58,50 @@ def instance():
 
 @pytest.fixture
 def mocked_request():
-    with patch("requests.get", new=requests_get_mock):
+    with patch("requests.Session.get", new=requests_get_mock):
         yield
 
 
 @pytest.fixture
 def mocked_auth_request():
-    def requests_auth_get(*args, **kwargs):
+    def requests_auth_get(session, *args, **kwargs):
         # Make sure we're passing in authentication
-        assert 'auth' in kwargs, 'Missing "auth" argument in requests.get(...) call'
+        assert 'auth' in kwargs, 'Missing "auth" argument in requests.Session.get(...) call'
 
         # Make sure we've got the correct username and password
-        assert kwargs['auth'] == (TEST_USERNAME, TEST_PASSWORD), "Incorrect username or password in requests.get"
+        assert kwargs['auth'] == (
+            TEST_USERNAME,
+            TEST_PASSWORD,
+        ), "Incorrect username or password in requests.Session.get"
 
         # Return mocked request.get(...)
-        return requests_get_mock(*args, **kwargs)
+        return requests_get_mock(session, *args, **kwargs)
 
-    with patch("requests.get", new=requests_auth_get):
+    with patch("requests.Session.get", new=requests_auth_get):
         yield
 
 
 @pytest.fixture
 def mocked_bad_cert_request():
     """
-    Mock request.get to an endpoint with a badly configured ssl cert
+    Mock request.Session.get to an endpoint with a badly configured ssl cert
     """
 
-    def requests_bad_cert_get(*args, **kwargs):
+    def requests_bad_cert_get(session, *args, **kwargs):
         # Make sure we're passing in the 'verify' argument
-        assert 'verify' in kwargs, 'Missing "verify" argument in requests.get(...) call'
+        assert 'verify' in kwargs, 'Missing "verify" argument in requests.Session.get(...) call'
 
         if kwargs['verify']:
             raise SSLError("certificate verification failed for {}".format(args[0]))
 
         # Return the actual response
-        return requests_get_mock(*args, **kwargs)
+        return requests_get_mock(session, *args, **kwargs)
 
-    with patch("requests.get", new=requests_bad_cert_get):
+    with patch("requests.Session.get", new=requests_bad_cert_get):
         yield
 
 
-def requests_get_mock(*args, **kwargs):
+def requests_get_mock(session, *args, **kwargs):
     if args[0] == YARN_CLUSTER_METRICS_URL:
         return MockResponse(file_path=os.path.join(FIXTURE_DIR, 'cluster_metrics'))
     elif args[0] == YARN_APPS_URL: