diff --git a/lib/mix/tasks/phoenix_kit.install.ex b/lib/mix/tasks/phoenix_kit.install.ex
index 23c43a078..4ad875c35 100644
--- a/lib/mix/tasks/phoenix_kit.install.ex
+++ b/lib/mix/tasks/phoenix_kit.install.ex
@@ -135,18 +135,40 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
         # CRITICAL: Check if required configuration exists BEFORE starting app
         # This prevents configuration timing issues where config is added via Igniter
         # but the app has already started with cached (missing) configuration
+
+        # Check if this is a retry pass (automatic restart after adding config)
+        is_retry = Process.get(:phoenix_kit_retry_pass, false)
         config_status = check_required_configuration()
 
-        case config_status do
-          :missing ->
+        case {config_status, is_retry} do
+          {:missing, false} ->
             # First pass: Add configuration via Igniter without starting app
+            # Store status in Process dictionary for tracking
+            Process.put(:phoenix_kit_config_status, :missing)
+
             show_missing_config_message(argv)
-            result = super(argv)
-            show_config_added_message(argv)
-            result
+            super(argv)
+
+            # AUTOMATIC RESTART instead of asking user to run again manually
+            Mix.shell().info("""
+
+            ✅ Configuration added successfully!
+            🔄 Automatically restarting to complete the installation...
+            """)
 
-          :ok ->
+            # Clean Process dictionary to ensure fresh state for retry
+            Process.delete(:phoenix_kit_config_status)
+
+            # Mark this as a retry pass to prevent infinite loops
+            Process.put(:phoenix_kit_retry_pass, true)
+
+            # Recursive call with same arguments - automatic restart
+            run(argv)
+
+          {:ok, _} ->
             # Second pass: Configuration exists, safe to start app and complete installation
+            Process.put(:phoenix_kit_config_status, :ok)
+
             # Run standard igniter process
             result = super(argv)
 
@@ -158,7 +180,27 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
               AssetRebuild.check_and_rebuild(verbose: true)
             end
 
+            # Clean up retry flag on successful completion
+            Process.delete(:phoenix_kit_retry_pass)
             result
+
+          {:missing, true} ->
+            # Safety check: Configuration still missing after automatic retry
+            # This prevents infinite loops if configuration addition fails
+            Mix.shell().error("""
+
+            ❌ Configuration was not added successfully after automatic retry.
+
+            Please check config/config.exs manually and ensure it contains:
+            - config :ueberauth, Ueberauth (with providers: %{})
+            - config :hammer (with backend and expiry_ms)
+            - config :phoenix_kit, Oban (with queues configuration)
+
+            Then run: mix phoenix_kit.install #{Enum.join(argv, " ")}
+            """)
+
+            Process.delete(:phoenix_kit_retry_pass)
+            :error
         end
       end
     end
@@ -286,17 +328,6 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
       """)
     end
 
-    # Display message after configuration is added
-    defp show_config_added_message(argv) do
-      Mix.shell().info("""
-
-      ✅ Configuration added successfully!
-
-      Next step: Run the install command again to complete the installation:
-        mix phoenix_kit.install #{Enum.join(argv, " ")}
-      """)
-    end
-
     # Check if all required configuration exists
     # Returns :ok if all config present, :missing if any config is missing
     defp check_required_configuration do
@@ -361,9 +392,9 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
       has_oban_config =
         Enum.any?(lines, fn line ->
           trimmed = String.trim(line)
-          # Not a comment and contains config :phoenix_kit, Oban
+          # Not a comment and contains config :any_app, Oban
           !String.starts_with?(trimmed, "#") and
-            String.contains?(line, "config :phoenix_kit, Oban")
+            String.contains?(line, ", Oban")
         end)
 
       has_queues =
diff --git a/lib/mix/tasks/phoenix_kit.status.ex b/lib/mix/tasks/phoenix_kit.status.ex
index f3aee7abd..6189f4ee9 100644
--- a/lib/mix/tasks/phoenix_kit.status.ex
+++ b/lib/mix/tasks/phoenix_kit.status.ex
@@ -60,24 +60,15 @@ defmodule Mix.Tasks.PhoenixKit.Status do
   ]
 
   def run(argv) do
-    # Conditionally start the application if repositories aren't available
-    app_started_by_us = ensure_app_started()
-
-    try do
-      {opts, _argv, _errors} = OptionParser.parse(argv, switches: @switches, aliases: @aliases)
-
-      prefix = opts[:prefix] || "public"
-      verbose = opts[:verbose] || false
-
-      show_comprehensive_status(prefix, verbose)
-    after
-      # Stop the application if we started it
-      if app_started_by_us do
-        # Note: Mix doesn't have app.stop task, and typically apps stay running
-        # This is normal behavior for Mix tasks
-        :ok
-      end
-    end
+    # Start the application to ensure repo is available
+    Mix.Task.run("app.start")
+
+    {opts, _argv, _errors} = OptionParser.parse(argv, switches: @switches, aliases: @aliases)
+
+    prefix = opts[:prefix] || "public"
+    verbose = opts[:verbose] || false
+
+    show_comprehensive_status(prefix, verbose)
   end
 
   # Main status display function
@@ -526,29 +517,6 @@ defmodule Mix.Tasks.PhoenixKit.Status do
     _ -> false
   end
 
-  # Ensure application is started only if needed
-  # Returns true if we started the app, false if it was already running
-  defp ensure_app_started do
-    # Check if we can get repo configuration
-    case get_repo_with_fallback() do
-      nil ->
-        # No repo found, start app and try again
-        Mix.Task.run("app.start")
-        true
-
-      repo ->
-        # Repo found, check if it's actually available
-        if repo_available?(repo) do
-          # Repo is available, no need to start app
-          false
-        else
-          # Repo not available, start app
-          Mix.Task.run("app.start")
-          true
-        end
-    end
-  end
-
   # Pad version number for consistent display
   defp pad_version(version) when version < 10, do: "0#{version}"
   defp pad_version(version), do: to_string(version)
diff --git a/lib/mix/tasks/phoenix_kit.update.ex b/lib/mix/tasks/phoenix_kit.update.ex
index 0fdeec72a..c5fee6650 100644
--- a/lib/mix/tasks/phoenix_kit.update.ex
+++ b/lib/mix/tasks/phoenix_kit.update.ex
@@ -167,26 +167,60 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
           # CRITICAL: Check if required configuration exists BEFORE starting app
           # This prevents configuration timing issues where config is added via Igniter
           # but the app has already started with cached (missing) configuration
+
+          # Check if this is a retry pass (automatic restart after adding config)
+          is_retry = Process.get(:phoenix_kit_retry_pass, false)
           config_status = check_required_configuration()
 
-          case config_status do
-            :missing ->
+          case {config_status, is_retry} do
+            {:missing, false} ->
               # First pass: Add configuration via Igniter without starting app
               # Store config status in Process dictionary for igniter/1 to read
               Process.put(:phoenix_kit_config_status, :missing)
               show_missing_config_message(argv)
-              result = super(argv)
-              show_config_added_message(argv)
-              result
+              super(argv)
+
+              # Automatic restart instead of manual prompt
+              Mix.shell().info("""
+
+              ✅ Configuration added successfully!
+              🔄 Automatically restarting to complete the update...
+              """)
 
-            :ok ->
-              # Second pass: Configuration exists, safe to start app and update
+              # Clean Process dictionary for fresh state
+              Process.delete(:phoenix_kit_config_status)
+              Process.put(:phoenix_kit_retry_pass, true)
+
+              # Recursive call with same arguments
+              run(argv)
+
+            {:ok, _} ->
+              # Second pass (automatic or manual): Configuration exists, safe to start app
               # Store config status in Process dictionary for igniter/1 to read
               Process.put(:phoenix_kit_config_status, :ok)
               Mix.Task.run("app.start")
               result = super(argv)
               post_igniter_tasks(elem(opts, 0))
+
+              # Clean retry flag
+              Process.delete(:phoenix_kit_retry_pass)
               result
+
+            {:missing, true} ->
+              # Safety: Configuration still missing after retry
+              Mix.shell().error("""
+
+              ❌ Configuration was not added successfully after automatic retry.
+
+              This may indicate a problem with your config/config.exs file.
+              Please check the file manually and ensure it's writable.
+
+              Then run manually:
+                mix phoenix_kit.update #{Enum.join(argv, " ")}
+              """)
+
+              Process.delete(:phoenix_kit_retry_pass)
+              :error
           end
         end
       end
@@ -201,6 +235,7 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
       PhoenixKit requires configuration for:
       - Ueberauth (OAuth authentication)
       - Hammer (rate limiting)
+      - Oban (background jobs for file processing)
 
       This configuration will be added now.
 
@@ -209,17 +244,6 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
       """)
     end
 
-    # Display message after configuration is added
-    defp show_config_added_message(argv) do
-      Mix.shell().info("""
-
-      ✅ Configuration added successfully!
-
-      Next step: Run the update command again to complete the upgrade:
-        mix phoenix_kit.update #{Enum.join(argv, " ")}
-      """)
-    end
-
     # Check if all required configuration exists
     # Returns :ok if all config present, :missing if any config is missing
     defp check_required_configuration do
@@ -284,9 +308,10 @@ if Code.ensure_loaded?(Igniter.Mix.Task) do
       has_oban_config =
         Enum.any?(lines, fn line ->
           trimmed = String.trim(line)
-          # Not a comment and contains config :phoenix_kit, Oban
+          # Not a comment and contains config for any app with Oban
+          # Matches: "config :any_app, Oban" or "config :any_app, Oban,"
           !String.starts_with?(trimmed, "#") and
-            String.contains?(line, "config :phoenix_kit, Oban")
+            String.contains?(line, ", Oban")
         end)
 
       has_queues =
diff --git a/mix.exs b/mix.exs
index 66a80709f..03d8a52fa 100644
--- a/mix.exs
+++ b/mix.exs
@@ -128,6 +128,8 @@ defmodule PhoenixKit.MixProject do
       {:finch, "~> 0.18"},
 
       # Code generation and project patching
+      # Note: Available in all environments for library code, but typically
+      # only needed in :dev when used as a dependency in parent projects
       {:igniter, "~> 0.7"}
     ]
   end