diff --git a/lib/rabbitmq/cli/plugins/commands/directories_command.ex b/lib/rabbitmq/cli/plugins/commands/directories_command.ex
index aa5f1058..b4f8714c 100644
--- a/lib/rabbitmq/cli/plugins/commands/directories_command.ex
+++ b/lib/rabbitmq/cli/plugins/commands/directories_command.ex
@@ -71,8 +71,14 @@ defmodule RabbitMQ.CLI.Plugins.Commands.DirectoriesCommand do
   end
 
   def run([], %{offline: true} = opts) do
-    do_run(fn key ->
-      Config.get_option(key, opts)
+    do_run(fn
+      :enabled_plugins_file ->
+        case PluginHelpers.enabled_plugins_file(opts) do
+          {:ok, plugins_file} -> plugins_file
+          _ -> nil
+        end
+      key ->
+        Config.get_option(key, opts)
     end)
   end
 
diff --git a/lib/rabbitmq/cli/plugins/plugins_helpers.ex b/lib/rabbitmq/cli/plugins/plugins_helpers.ex
index c423268a..ca712282 100644
--- a/lib/rabbitmq/cli/plugins/plugins_helpers.ex
+++ b/lib/rabbitmq/cli/plugins/plugins_helpers.ex
@@ -70,17 +70,44 @@ defmodule RabbitMQ.CLI.Plugins.Helpers do
     end
   end
 
+  @spec enabled_plugins_file(map()) :: {:ok, charlist()} | {:error, any()}
   def enabled_plugins_file(opts) do
     case Config.get_option(:enabled_plugins_file, opts) do
-      nil -> {:error, :no_plugins_file}
-      file -> {:ok, file}
+      nil ->
+        case :os.type do
+          {:unix, _} ->
+            sys_prefix = System.get_env("SYS_PREFIX", "/")
+            config_base_dir = Path.join([sys_prefix, "etc", "rabbitmq"])
+            data_dir = Path.join([sys_prefix, "var", "lib", "rabbitmq"])
+            legacy_location = Path.absname(Path.join([config_base_dir, "enabled_plugins"]))
+            modern_location = Path.absname(Path.join([data_dir, "enabled_plugins"]))
+            case {File.exists?(modern_location), File.exists?(legacy_location)} do
+              {false, true} ->
+                {:ok, legacy_location}
+              _ ->
+                {:ok, modern_location}
+            end
+          {:win32, _} ->
+            rabbitmq_base = case System.fetch_env("RABBITMQ_BASE") do
+                              {:ok, Value} ->
+                                Value
+                              _ ->
+                                app_data = System.get_env("APPDATA")
+                                Path.join([app_data, "RabbitMQ"])
+                            end
+            {:ok, Path.join([rabbitmq_base, "enabled_plugins"])}
+        end
+      file ->
+        {:ok, file}
     end
   end
 
+  @spec enabled_plugins_file(any(), map()) :: {:ok, charlist()} | {:error, any()}
   def enabled_plugins_file(_, opts) do
     enabled_plugins_file(opts)
   end
 
+  @spec set_enabled_plugins([atom()], map()) :: {:ok, Enumerable.t()} | {:error, any()}
   def set_enabled_plugins(plugins, opts) do
     plugin_atoms = :lists.usort(for plugin <- plugins, do: to_atom(plugin))
     require_rabbit_and_plugins(opts)
@@ -89,11 +116,11 @@ defmodule RabbitMQ.CLI.Plugins.Helpers do
   end
 
   @spec update_enabled_plugins(
-          [atom()],
-          :online | :offline | :best_effort,
-          node(),
-          map()
-        ) :: map() | {:error, any()}
+    [atom()],
+    :online | :offline | :best_effort,
+    node(),
+    map()
+  ) :: map() | {:error, any()}
   def update_enabled_plugins(enabled_plugins, mode, node_name, opts) do
     {:ok, plugins_file} = enabled_plugins_file(opts)
 
diff --git a/test/plugins/directories_command_test.exs b/test/plugins/directories_command_test.exs
index 9c431b67..6cf2d1e0 100644
--- a/test/plugins/directories_command_test.exs
+++ b/test/plugins/directories_command_test.exs
@@ -23,9 +23,6 @@ defmodule DirectoriesCommandTest do
     RabbitMQ.CLI.Core.Distribution.start()
     node = get_rabbit_hostname()
 
-    {:ok, plugins_file} = :rabbit_misc.rpc_call(node,
-                                                :application, :get_env,
-                                                [:rabbit, :enabled_plugins_file])
     {:ok, plugins_dir} = :rabbit_misc.rpc_call(node,
                                                :application, :get_env,
                                                [:rabbit, :plugins_dir])
@@ -36,7 +33,7 @@ defmodule DirectoriesCommandTest do
     rabbitmq_home = :rabbit_misc.rpc_call(node, :code, :lib_dir, [:rabbit])
 
     {:ok, opts: %{
-        plugins_file: plugins_file,
+        plugins_file: nil,
         plugins_dir: plugins_dir,
         plugins_expand_dir: plugins_expand_dir,
         rabbitmq_home: rabbitmq_home,
@@ -100,12 +97,52 @@ defmodule DirectoriesCommandTest do
     assert @command.validate_execution_environment([], opts) == :ok
   end
 
-
   test "run: when --online is used, lists plugin directories", context do
     opts = Map.merge(context[:opts], %{online: true})
+
+    {:ok, plugins_file} = :rabbit_misc.rpc_call(Map.get(opts, :node),
+                                                :application, :get_env,
+                                                [:rabbit, :enabled_plugins_file])
+
     dirs = %{plugins_dir: to_string(Map.get(opts, :plugins_dir)),
              plugins_expand_dir: to_string(Map.get(opts, :plugins_expand_dir)),
-             enabled_plugins_file: to_string(Map.get(opts, :plugins_file))}
+             enabled_plugins_file: to_string(plugins_file)}
+
+    assert @command.run([], opts) == {:ok, dirs}
+  end
+
+  test "run: when --offline is used, checks for enabled_plugins in the data dir, falling back to the config dir", context do
+    sys_prefix = Path.join([System.tmp_dir(), "DirectoriesCommandTest"])
+
+    System.put_env("SYS_PREFIX", sys_prefix)
+
+    config_dir = Path.join([sys_prefix, "etc", "rabbitmq"])
+    legacy_file = Path.join([config_dir, "enabled_plugins"])
+
+    data_dir = Path.join([sys_prefix, "var", "lib", "rabbitmq"])
+    modern_file = Path.join([data_dir, "enabled_plugins"])
+
+    File.rm(legacy_file)
+    File.rm(modern_file)
+
+    refute File.exists?(legacy_file)
+    refute File.exists?(modern_file)
+
+    opts = Map.merge(context[:opts], %{offline: true})
+
+    dirs = %{plugins_dir: to_string(Map.get(opts, :plugins_dir)),
+             plugins_expand_dir: to_string(Map.get(opts, :plugins_expand_dir)),
+             enabled_plugins_file: modern_file}
+
+    assert @command.run([], opts) == {:ok, dirs}
+
+    :ok = File.mkdir_p(config_dir)
+    :ok = File.touch(legacy_file)
+
+    assert @command.run([], opts) == {:ok, Map.merge(dirs, %{enabled_plugins_file: legacy_file})}
+
+    :ok = File.mkdir_p(data_dir)
+    :ok = File.touch(modern_file)
 
     assert @command.run([], opts) == {:ok, dirs}
   end