diff --git a/src/sentry/integrations/jira/integration.py b/src/sentry/integrations/jira/integration.py
index a0e20abcf8a222..441da6bf7c7b9d 100644
--- a/src/sentry/integrations/jira/integration.py
+++ b/src/sentry/integrations/jira/integration.py
@@ -15,6 +15,7 @@
 
 from sentry import features
 from sentry.eventstore.models import GroupEvent
+from sentry.exceptions import InvalidConfiguration
 from sentry.integrations.base import (
     FeatureDescription,
     IntegrationData,
@@ -1006,17 +1007,27 @@ def sync_assignee_outbound(
                     extra={
                         "integration_id": external_issue.integration_id,
                         "user_id": user.id,
+                        "user_emails": user.emails,
                         "issue_key": external_issue.key,
+                        "organization_id": external_issue.organization_id,
                     },
                 )
-                return
+                if not user.emails:
+                    raise InvalidConfiguration(
+                        {
+                            "email": "User must have a verified email on Sentry to sync assignee in Jira",
+                            "help": "https://sentry.io/settings/account/emails",
+                        }
+                    )
+                raise InvalidConfiguration({"email": "Unable to find the requested user"})
         try:
             id_field = client.user_id_field()
             client.assign_issue(external_issue.key, jira_user and jira_user.get(id_field))
-        except (ApiUnauthorized, ApiError):
+        except ApiError as e:
             # TODO(jess): do we want to email people about these types of failures?
             logger.info(
                 "jira.failed-to-assign",
+                exc_info=e,
                 extra={
                     "organization_id": external_issue.organization_id,
                     "integration_id": external_issue.integration_id,
@@ -1024,6 +1035,7 @@ def sync_assignee_outbound(
                     "issue_key": external_issue.key,
                 },
             )
+            raise
 
     def sync_status_outbound(
         self, external_issue: ExternalIssue, is_resolved: bool, project_id: int
diff --git a/src/sentry/integrations/tasks/sync_assignee_outbound.py b/src/sentry/integrations/tasks/sync_assignee_outbound.py
index 0d796c47d34d7b..d1b8f0eda09acb 100644
--- a/src/sentry/integrations/tasks/sync_assignee_outbound.py
+++ b/src/sentry/integrations/tasks/sync_assignee_outbound.py
@@ -2,6 +2,7 @@
 
 from sentry import analytics, features
 from sentry.constants import ObjectStatus
+from sentry.exceptions import InvalidConfiguration
 from sentry.integrations.errors import OrganizationIntegrationNotFound
 from sentry.integrations.models.external_issue import ExternalIssue
 from sentry.integrations.models.integration import Integration
@@ -12,7 +13,7 @@
 from sentry.integrations.services.assignment_source import AssignmentSource
 from sentry.integrations.services.integration import integration_service
 from sentry.models.organization import Organization
-from sentry.shared_integrations.exceptions import IntegrationError
+from sentry.shared_integrations.exceptions import ApiUnauthorized, IntegrationError
 from sentry.silo.base import SiloMode
 from sentry.tasks.base import instrumented_task, retry
 from sentry.taskworker.config import TaskworkerConfig
@@ -96,5 +97,5 @@ def sync_assignee_outbound(
                     id=integration.id,
                     organization_id=external_issue.organization_id,
                 )
-        except OrganizationIntegrationNotFound:
-            lifecycle.record_halt("organization_integration_not_found")
+        except (OrganizationIntegrationNotFound, ApiUnauthorized, InvalidConfiguration) as e:
+            lifecycle.record_halt(halt_reason=e)
diff --git a/tests/sentry/integrations/jira/test_integration.py b/tests/sentry/integrations/jira/test_integration.py
index afb19c471922eb..96bcbf70004245 100644
--- a/tests/sentry/integrations/jira/test_integration.py
+++ b/tests/sentry/integrations/jira/test_integration.py
@@ -9,6 +9,7 @@
 
 from fixtures.integrations.jira.stub_client import StubJiraApiClient
 from fixtures.integrations.stub_service import StubService
+from sentry.exceptions import InvalidConfiguration
 from sentry.integrations.jira.integration import JiraIntegrationProvider
 from sentry.integrations.jira.views import SALT
 from sentry.integrations.models.external_issue import ExternalIssue
@@ -824,7 +825,8 @@ def test_sync_assignee_outbound_no_email(self):
             "https://example.atlassian.net/rest/api/2/user/assignable/search",
             json=[{"accountId": "deadbeef123", "displayName": "Dead Beef"}],
         )
-        installation.sync_assignee_outbound(external_issue, user)
+        with pytest.raises(InvalidConfiguration):
+            installation.sync_assignee_outbound(external_issue, user)
 
         # No sync made as jira users don't have email addresses
         assert len(responses.calls) == 1
diff --git a/tests/sentry/integrations/tasks/test_sync_assignee_outbound.py b/tests/sentry/integrations/tasks/test_sync_assignee_outbound.py
index 16d2c75c78154c..ea36b6ba958a44 100644
--- a/tests/sentry/integrations/tasks/test_sync_assignee_outbound.py
+++ b/tests/sentry/integrations/tasks/test_sync_assignee_outbound.py
@@ -2,12 +2,13 @@
 
 import pytest
 
+from sentry.integrations.errors import OrganizationIntegrationNotFound
 from sentry.integrations.example import ExampleIntegration
 from sentry.integrations.models import ExternalIssue, Integration
 from sentry.integrations.models.organization_integration import OrganizationIntegration
 from sentry.integrations.tasks import sync_assignee_outbound
 from sentry.integrations.types import EventLifecycleOutcome
-from sentry.testutils.asserts import assert_success_metric
+from sentry.testutils.asserts import assert_halt_metric, assert_success_metric
 from sentry.testutils.cases import TestCase
 from sentry.testutils.silo import assume_test_silo_mode_of
 from sentry.users.services.user import RpcUser
@@ -151,4 +152,6 @@ def test_missing_organization_integration(self, mock_sync_assignee, mock_record_
         mock_sync_assignee.assert_not_called()
 
         assert mock_record_event.call_count == 2
-        assert_success_metric(mock_record_event)
+        assert_halt_metric(
+            mock_record_event, OrganizationIntegrationNotFound("missing org_integration")
+        )