diff --git a/docs/cli/settings.md b/docs/cli/settings.md
index d2680d65ad..cdd904896d 100644
--- a/docs/cli/settings.md
+++ b/docs/cli/settings.md
@@ -22,18 +22,19 @@ they appear in the UI.
 
 ### General
 
-| UI Label                | Setting                            | Description                                                                                                                                                                    | Default     |
-| ----------------------- | ---------------------------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | ----------- |
-| Vim Mode                | `general.vimMode`                  | Enable Vim keybindings                                                                                                                                                         | `false`     |
-| Default Approval Mode   | `general.defaultApprovalMode`      | The default approval mode for tool execution. 'default' prompts for approval, 'auto_edit' auto-approves edit tools, and 'plan' is read-only mode. 'yolo' is not supported yet. | `"default"` |
-| Enable Auto Update      | `general.enableAutoUpdate`         | Enable automatic updates.                                                                                                                                                      | `true`      |
-| Enable Notifications    | `general.enableNotifications`      | Enable run-event notifications for action-required prompts and session completion. Currently macOS only.                                                                       | `false`     |
-| Plan Directory          | `general.plan.directory`           | The directory where planning artifacts are stored. If not specified, defaults to the system temporary directory.                                                               | `undefined` |
-| Plan Model Routing      | `general.plan.modelRouting`        | Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pro for the planning phase and Flash for the implementation phase.                           | `true`      |
-| Max Chat Model Attempts | `general.maxAttempts`              | Maximum number of attempts for requests to the main chat model. Cannot exceed 10.                                                                                              | `10`        |
-| Debug Keystroke Logging | `general.debugKeystrokeLogging`    | Enable debug logging of keystrokes to the console.                                                                                                                             | `false`     |
-| Enable Session Cleanup  | `general.sessionRetention.enabled` | Enable automatic session cleanup                                                                                                                                               | `true`      |
-| Keep chat history       | `general.sessionRetention.maxAge`  | Automatically delete chats older than this time period (e.g., "30d", "7d", "24h", "1w")                                                                                        | `"30d"`     |
+| UI Label                       | Setting                               | Description                                                                                                                                                                    | Default     |
+| ------------------------------ | ------------------------------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | ----------- |
+| Vim Mode                       | `general.vimMode`                     | Enable Vim keybindings                                                                                                                                                         | `false`     |
+| Default Approval Mode          | `general.defaultApprovalMode`         | The default approval mode for tool execution. 'default' prompts for approval, 'auto_edit' auto-approves edit tools, and 'plan' is read-only mode. 'yolo' is not supported yet. | `"default"` |
+| Enable Auto Update             | `general.enableAutoUpdate`            | Enable automatic updates.                                                                                                                                                      | `true`      |
+| Enable Notifications           | `general.enableNotifications`         | Enable run-event notifications for action-required prompts and session completion. Currently macOS only.                                                                       | `false`     |
+| Plan Directory                 | `general.plan.directory`              | The directory where planning artifacts are stored. If not specified, defaults to the system temporary directory.                                                               | `undefined` |
+| Plan Model Routing             | `general.plan.modelRouting`           | Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pro for the planning phase and Flash for the implementation phase.                           | `true`      |
+| Clear Context on Plan Approval | `general.plan.clearContextOnApproval` | Automatically clear conversation context after a plan is approved and implementation begins.                                                                                   | `undefined` |
+| Max Chat Model Attempts        | `general.maxAttempts`                 | Maximum number of attempts for requests to the main chat model. Cannot exceed 10.                                                                                              | `10`        |
+| Debug Keystroke Logging        | `general.debugKeystrokeLogging`       | Enable debug logging of keystrokes to the console.                                                                                                                             | `false`     |
+| Enable Session Cleanup         | `general.sessionRetention.enabled`    | Enable automatic session cleanup                                                                                                                                               | `true`      |
+| Keep chat history              | `general.sessionRetention.maxAge`     | Automatically delete chats older than this time period (e.g., "30d", "7d", "24h", "1w")                                                                                        | `"30d"`     |
 
 ### Output
 
diff --git a/docs/reference/configuration.md b/docs/reference/configuration.md
index 1f1299072b..1929a56a8e 100644
--- a/docs/reference/configuration.md
+++ b/docs/reference/configuration.md
@@ -143,6 +143,11 @@ their corresponding top-level category object in your `settings.json` file.
     implementation phase.
   - **Default:** `true`
 
+- **`general.plan.clearContextOnApproval`** (boolean):
+  - **Description:** Automatically clear conversation context after a plan is
+    approved and implementation begins.
+  - **Default:** `undefined`
+
 - **`general.retryFetchErrors`** (boolean):
   - **Description:** Retry on "exception TypeError: fetch failed sending
     request" errors.
diff --git a/schemas/settings.schema.json b/schemas/settings.schema.json
index 36816079ca..318fc72446 100644
--- a/schemas/settings.schema.json
+++ b/schemas/settings.schema.json
@@ -124,6 +124,12 @@
               "markdownDescription": "Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pro for the planning phase and Flash for the implementation phase.\n\n- Category: `General`\n- Requires restart: `no`\n- Default: `true`",
               "default": true,
               "type": "boolean"
+            },
+            "clearContextOnApproval": {
+              "title": "Clear Context on Plan Approval",
+              "description": "Automatically clear conversation context after a plan is approved and implementation begins.",
+              "markdownDescription": "Automatically clear conversation context after a plan is approved and implementation begins.\n\n- Category: `General`\n- Requires restart: `no`",
+              "type": "boolean"
             }
           },
           "additionalProperties": false