diff --git a/packages/cli/src/ui/commands/initCommand.test.ts b/packages/cli/src/ui/commands/initCommand.test.ts
index 1130c5b3..3ed32d8e 100644
--- a/packages/cli/src/ui/commands/initCommand.test.ts
+++ b/packages/cli/src/ui/commands/initCommand.test.ts
@@ -53,7 +53,7 @@ describe('initCommand', () => {
     vi.clearAllMocks();
   });
 
-  it(`should inform the user if ${DEFAULT_CONTEXT_FILENAME} already exists and is non-empty`, async () => {
+  it(`should ask for confirmation if ${DEFAULT_CONTEXT_FILENAME} already exists and is non-empty`, async () => {
     // Arrange: Simulate that the file exists
     vi.mocked(fs.existsSync).mockReturnValue(true);
     vi.spyOn(fs, 'readFileSync').mockReturnValue('# Existing content');
@@ -61,13 +61,15 @@ describe('initCommand', () => {
     // Act: Run the command's action
     const result = await initCommand.action!(mockContext, '');
 
-    // Assert: Check for the correct informational message
-    expect(result).toEqual({
-      type: 'message',
-      messageType: 'info',
-      content: `A ${DEFAULT_CONTEXT_FILENAME} file already exists in this directory. No changes were made.`,
-    });
-    // Assert: Ensure no file was written
+    // Assert: Check for the correct confirmation request
+    expect(result).toEqual(
+      expect.objectContaining({
+        type: 'confirm_action',
+        prompt: expect.anything(), // React element, not a string
+        originalInvocation: expect.anything(),
+      }),
+    );
+    // Assert: Ensure no file was written yet
     expect(fs.writeFileSync).not.toHaveBeenCalled();
   });
 
@@ -91,9 +93,13 @@ describe('initCommand', () => {
     );
 
     // Assert: Check that the correct prompt is submitted
-    expect(result.type).toBe('submit_prompt');
-    expect(result.content).toContain(
-      'You are Qwen Code, an interactive CLI agent',
+    expect(result).toEqual(
+      expect.objectContaining({
+        type: 'submit_prompt',
+        content: expect.stringContaining(
+          'You are Qwen Code, an interactive CLI agent',
+        ),
+      }),
     );
   });
 
@@ -104,7 +110,43 @@ describe('initCommand', () => {
     const result = await initCommand.action!(mockContext, '');
 
     expect(fs.writeFileSync).toHaveBeenCalledWith(geminiMdPath, '', 'utf8');
-    expect(result.type).toBe('submit_prompt');
+    expect(result).toEqual(
+      expect.objectContaining({
+        type: 'submit_prompt',
+      }),
+    );
+  });
+
+  it(`should regenerate ${DEFAULT_CONTEXT_FILENAME} when overwrite is confirmed`, async () => {
+    // Arrange: Simulate that the file exists and overwrite is confirmed
+    vi.mocked(fs.existsSync).mockReturnValue(true);
+    vi.spyOn(fs, 'readFileSync').mockReturnValue('# Existing content');
+    mockContext.overwriteConfirmed = true;
+
+    // Act: Run the command's action
+    const result = await initCommand.action!(mockContext, '');
+
+    // Assert: Check that writeFileSync was called correctly
+    expect(fs.writeFileSync).toHaveBeenCalledWith(geminiMdPath, '', 'utf8');
+
+    // Assert: Check that an informational message was added to the UI
+    expect(mockContext.ui.addItem).toHaveBeenCalledWith(
+      {
+        type: 'info',
+        text: `Empty ${DEFAULT_CONTEXT_FILENAME} created. Now analyzing the project to populate it.`,
+      },
+      expect.any(Number),
+    );
+
+    // Assert: Check that the correct prompt is submitted
+    expect(result).toEqual(
+      expect.objectContaining({
+        type: 'submit_prompt',
+        content: expect.stringContaining(
+          'You are Qwen Code, an interactive CLI agent',
+        ),
+      }),
+    );
   });
 
   it('should return an error if config is not available', async () => {
diff --git a/packages/cli/src/ui/commands/initCommand.ts b/packages/cli/src/ui/commands/initCommand.ts
index 3d90db3c..efec93f1 100644
--- a/packages/cli/src/ui/commands/initCommand.ts
+++ b/packages/cli/src/ui/commands/initCommand.ts
@@ -1,6 +1,6 @@
 /**
  * @license
- * Copyright 2025 Google LLC
+ * Copyright 2025 Qwen
  * SPDX-License-Identifier: Apache-2.0
  */
 
@@ -13,6 +13,8 @@ import {
   CommandKind,
 } from './types.js';
 import { getCurrentGeminiMdFilename } from '@qwen-code/qwen-code-core';
+import { Text } from 'ink';
+import React from 'react';
 
 export const initCommand: SlashCommand = {
   name: 'init',
@@ -35,15 +37,27 @@ export const initCommand: SlashCommand = {
 
     try {
       if (fs.existsSync(contextFilePath)) {
-        // If file exists but is empty (or whitespace), continue to initialize; otherwise, bail out
+        // If file exists but is empty (or whitespace), continue to initialize
         try {
           const existing = fs.readFileSync(contextFilePath, 'utf8');
           if (existing && existing.trim().length > 0) {
-            return {
-              type: 'message',
-              messageType: 'info',
-              content: `A ${contextFileName} file already exists in this directory. No changes were made.`,
-            };
+            // File exists and has content - ask for confirmation to overwrite
+            if (!context.overwriteConfirmed) {
+              return {
+                type: 'confirm_action',
+                // TODO: Move to .tsx file to use JSX syntax instead of React.createElement
+                // For now, using React.createElement to maintain .ts compatibility for PR review
+                prompt: React.createElement(
+                  Text,
+                  null,
+                  `A ${contextFileName} file already exists in this directory. Do you want to regenerate it?`,
+                ),
+                originalInvocation: {
+                  raw: context.invocation?.raw || '/init',
+                },
+              };
+            }
+            // User confirmed overwrite, continue with regeneration
           }
         } catch {
           // If we fail to read, conservatively proceed to (re)create the file