3 files changed, 26 insertions, 3 deletions
diff --git a/packages/cli/src/config/config.integration.test.ts b/packages/cli/src/config/config.integration.test.ts
index 4a965a1f..de329384 100644
--- a/packages/cli/src/config/config.integration.test.ts
+++ b/packages/cli/src/config/config.integration.test.ts
@@ -186,4 +186,22 @@ describe('Configuration Integration Tests', () => {
       expect(config.getFileFilteringRespectGitIgnore()).toBe(false);
     });
   });
+
+  describe('Checkpointing Configuration', () => {
+    it('should enable checkpointing when the setting is true', async () => {
+      const configParams: ConfigParameters = {
+        cwd: '/tmp',
+        contentGeneratorConfig: TEST_CONTENT_GENERATOR_CONFIG,
+        embeddingModel: 'test-embedding-model',
+        sandbox: false,
+        targetDir: tempDir,
+        debugMode: false,
+        checkpointing: true,
+      };
+
+      const config = new Config(configParams);
+
+      expect(config.getCheckpointingEnabled()).toBe(true);
+    });
+  });
 });
diff --git a/packages/cli/src/config/config.ts b/packages/cli/src/config/config.ts
index 6e52c6e2..afc63b78 100644
--- a/packages/cli/src/config/config.ts
+++ b/packages/cli/src/config/config.ts
@@ -49,7 +49,7 @@ interface CliArgs {
   show_memory_usage: boolean | undefined;
   yolo: boolean | undefined;
   telemetry: boolean | undefined;
-  checkpoint: boolean | undefined;
+  checkpointing: boolean | undefined;
   telemetryTarget: string | undefined;
   telemetryOtlpEndpoint: string | undefined;
   telemetryLogPrompts: boolean | undefined;
@@ -122,7 +122,7 @@ async function parseArguments(): Promise<CliArgs> {
       description:
         'Enable or disable logging of user prompts for telemetry. Overrides settings files.',
     })
-    .option('checkpoint', {
+    .option('checkpointing', {
       alias: 'c',
       type: 'boolean',
       description: 'Enables checkpointing of file edits',
@@ -229,7 +229,7 @@ export async function loadCliConfig(
     },
     // Git-aware file filtering settings
     fileFilteringRespectGitIgnore: settings.fileFiltering?.respectGitIgnore,
-    checkpoint: argv.checkpoint,
+    checkpointing: argv.checkpointing || settings.checkpointing?.enabled,
     proxy:
       process.env.HTTPS_PROXY ||
       process.env.https_proxy ||
diff --git a/packages/cli/src/config/settings.ts b/packages/cli/src/config/settings.ts
index a90ed2d8..b63f5bb6 100644
--- a/packages/cli/src/config/settings.ts
+++ b/packages/cli/src/config/settings.ts
@@ -27,6 +27,10 @@ export enum SettingScope {
   Workspace = 'Workspace',
 }
 
+export interface CheckpointingSettings {
+  enabled?: boolean;
+}
+
 export interface AccessibilitySettings {
   disableLoadingPhrases?: boolean;
 }
@@ -47,6 +51,7 @@ export interface Settings {
   telemetry?: TelemetrySettings;
   preferredEditor?: string;
   bugCommand?: BugCommandSettings;
+  checkpointing?: CheckpointingSettings;
 
   // Git-aware file filtering settings
   fileFiltering?: {