diff --git a/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.md b/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.md
index 523f9e64c..2136092ca 100644
--- a/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.md
+++ b/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.md
@@ -4,6 +4,36 @@ The actual snapshot is saved in `copilot.e2e.ts.snap`.
 
 Generated by [AVA](https://avajs.dev).
 
+## should be able to retry with api
+
+> should be able to list history after retry
+
+    [
+      {
+        messages: [
+          {
+            content: 'generate text to text',
+            role: 'assistant',
+          },
+        ],
+        tokens: 0,
+      },
+    ]
+
+> should be able to list history after retry
+
+    [
+      {
+        messages: [
+          {
+            content: 'generate text to text',
+            role: 'assistant',
+          },
+        ],
+        tokens: 0,
+      },
+    ]
+
 ## should be able to manage context
 
 > should list context files
@@ -13,14 +43,3 @@ Generated by [AVA](https://avajs.dev).
         id: 'docId1',
       },
     ]
-
-> should list context docs
-
-    [
-      {
-        blobId: 'fileId1',
-        chunkSize: 3,
-        name: 'sample.pdf',
-        status: 'finished',
-      },
-    ]
diff --git a/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.snap b/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.snap
index 2452b58a4..f186652f3 100644
Binary files a/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.snap and b/packages/backend/server/src/__tests__/__snapshots__/copilot.e2e.ts.snap differ
diff --git a/packages/backend/server/src/__tests__/__snapshots__/copilot.spec.ts.md b/packages/backend/server/src/__tests__/__snapshots__/copilot.spec.ts.md
new file mode 100644
index 000000000..4f239cbb4
--- /dev/null
+++ b/packages/backend/server/src/__tests__/__snapshots__/copilot.spec.ts.md
@@ -0,0 +1,151 @@
+# Snapshot report for `src/__tests__/copilot.spec.ts`
+
+The actual snapshot is saved in `copilot.spec.ts.snap`.
+
+Generated by [AVA](https://avajs.dev).
+
+## should revert message correctly
+
+> should have three messages before revert
+
+    [
+      {
+        content: 'hello world',
+        params: {
+          word: 'world',
+        },
+        role: 'system',
+      },
+      {
+        content: '1',
+        role: 'user',
+      },
+      {
+        content: '2',
+        role: 'assistant',
+      },
+      {
+        content: '3',
+        role: 'user',
+      },
+      {
+        content: '4',
+        role: 'assistant',
+      },
+    ]
+
+> should remove assistant message after revert
+
+    [
+      {
+        content: 'hello world',
+        params: {
+          word: 'world',
+        },
+        role: 'system',
+      },
+      {
+        content: '1',
+        role: 'user',
+      },
+      {
+        content: '2',
+        role: 'assistant',
+      },
+      {
+        content: '3',
+        role: 'user',
+      },
+    ]
+
+> should remove assistant message after revert
+
+    [
+      {
+        content: 'hello world',
+        params: {
+          word: 'world',
+        },
+        role: 'system',
+      },
+      {
+        content: '1',
+        role: 'user',
+      },
+      {
+        content: '2',
+        role: 'assistant',
+      },
+    ]
+
+> should have three messages before revert
+
+    [
+      {
+        content: 'hello world',
+        params: {
+          word: 'world',
+        },
+        role: 'system',
+      },
+      {
+        content: '1',
+        role: 'user',
+      },
+      {
+        content: '2',
+        role: 'assistant',
+      },
+      {
+        content: '3',
+        role: 'user',
+      },
+      {
+        content: '4',
+        role: 'assistant',
+      },
+    ]
+
+> should remove assistant message after revert
+
+    [
+      {
+        content: 'hello world',
+        params: {
+          word: 'world',
+        },
+        role: 'system',
+      },
+      {
+        content: '1',
+        role: 'user',
+      },
+      {
+        content: '2',
+        role: 'assistant',
+      },
+      {
+        content: '3',
+        role: 'user',
+      },
+    ]
+
+> should remove assistant message after revert
+
+    [
+      {
+        content: 'hello world',
+        params: {
+          word: 'world',
+        },
+        role: 'system',
+      },
+      {
+        content: '1',
+        role: 'user',
+      },
+      {
+        content: '2',
+        role: 'assistant',
+      },
+    ]
diff --git a/packages/backend/server/src/__tests__/__snapshots__/copilot.spec.ts.snap b/packages/backend/server/src/__tests__/__snapshots__/copilot.spec.ts.snap
new file mode 100644
index 000000000..516503db9
Binary files /dev/null and b/packages/backend/server/src/__tests__/__snapshots__/copilot.spec.ts.snap differ
diff --git a/packages/backend/server/src/__tests__/copilot.e2e.ts b/packages/backend/server/src/__tests__/copilot.e2e.ts
index 99cfc1f70..2d0da5ee2 100644
--- a/packages/backend/server/src/__tests__/copilot.e2e.ts
+++ b/packages/backend/server/src/__tests__/copilot.e2e.ts
@@ -498,6 +498,15 @@ test('should be able to retry with api', async t => {
     );
   }
 
+  const cleanObject = (obj: any[]) =>
+    JSON.parse(
+      JSON.stringify(obj, (k, v) =>
+        ['id', 'sessionId', 'createdAt'].includes(k) || v === null
+          ? undefined
+          : v
+      )
+    );
+
   // retry chat
   {
     const { id } = await createWorkspace(app);
@@ -514,10 +523,32 @@ test('should be able to retry with api', async t => {
 
     // should only have 1 message
     const histories = await getHistories(app, { workspaceId: id });
-    t.deepEqual(
-      histories.map(h => h.messages.map(m => m.content)),
-      [['generate text to text']],
-      'should be able to list history'
+    t.snapshot(
+      cleanObject(histories),
+      'should be able to list history after retry'
+    );
+  }
+
+  // retry chat with new message id
+  {
+    const { id } = await createWorkspace(app);
+    const sessionId = await createCopilotSession(
+      app,
+      id,
+      randomUUID(),
+      promptName
+    );
+    const messageId = await createCopilotMessage(app, sessionId);
+    await chatWithText(app, sessionId, messageId);
+    // retry with new message id
+    const newMessageId = await createCopilotMessage(app, sessionId);
+    await chatWithText(app, sessionId, newMessageId, '', true);
+
+    // should only have 1 message
+    const histories = await getHistories(app, { workspaceId: id });
+    t.snapshot(
+      cleanObject(histories),
+      'should be able to list history after retry'
     );
   }
 
diff --git a/packages/backend/server/src/__tests__/copilot.spec.ts b/packages/backend/server/src/__tests__/copilot.spec.ts
index 976e4e2de..85e435b63 100644
--- a/packages/backend/server/src/__tests__/copilot.spec.ts
+++ b/packages/backend/server/src/__tests__/copilot.spec.ts
@@ -602,36 +602,81 @@ test('should revert message correctly', async t => {
 
     const message = (await session.createMessage({
       sessionId,
-      content: 'hello',
+      content: '1',
     }))!;
 
     await s.pushByMessageId(message);
     await s.save();
   }
 
+  const cleanObject = (obj: any[]) =>
+    JSON.parse(
+      JSON.stringify(obj, (k, v) =>
+        ['id', 'createdAt'].includes(k) || v === null ? undefined : v
+      )
+    );
+
   // check ChatSession behavior
   {
     const s = (await session.get(sessionId))!;
-    s.push({ role: 'assistant', content: 'hi', createdAt: new Date() });
+    s.push({ role: 'assistant', content: '2', createdAt: new Date() });
+    s.push({ role: 'user', content: '3', createdAt: new Date() });
+    s.push({ role: 'assistant', content: '4', createdAt: new Date() });
     await s.save();
     const beforeRevert = s.finish({ word: 'world' });
-    t.is(beforeRevert.length, 3, 'should have three messages before revert');
+    t.snapshot(
+      cleanObject(beforeRevert),
+      'should have three messages before revert'
+    );
 
-    s.revertLatestMessage();
-    const afterRevert = s.finish({ word: 'world' });
-    t.is(afterRevert.length, 2, 'should remove assistant message after revert');
+    {
+      s.revertLatestMessage(false);
+      const afterRevert = s.finish({ word: 'world' });
+      t.snapshot(
+        cleanObject(afterRevert),
+        'should remove assistant message after revert'
+      );
+    }
+
+    {
+      s.revertLatestMessage(true);
+      const afterRevert = s.finish({ word: 'world' });
+      t.snapshot(
+        cleanObject(afterRevert),
+        'should remove assistant message after revert'
+      );
+    }
   }
 
   // check database behavior
   {
     let s = (await session.get(sessionId))!;
-    const beforeRevert = s.finish({ word: 'world' });
-    t.is(beforeRevert.length, 3, 'should have three messages before revert');
 
-    await session.revertLatestMessage(sessionId);
-    s = (await session.get(sessionId))!;
-    const afterRevert = s.finish({ word: 'world' });
-    t.is(afterRevert.length, 2, 'should remove assistant message after revert');
+    const beforeRevert = s.finish({ word: 'world' });
+    t.snapshot(
+      cleanObject(beforeRevert),
+      'should have three messages before revert'
+    );
+
+    {
+      await session.revertLatestMessage(sessionId, false);
+      s = (await session.get(sessionId))!;
+      const afterRevert = s.finish({ word: 'world' });
+      t.snapshot(
+        cleanObject(afterRevert),
+        'should remove assistant message after revert'
+      );
+    }
+
+    {
+      await session.revertLatestMessage(sessionId, true);
+      s = (await session.get(sessionId))!;
+      const afterRevert = s.finish({ word: 'world' });
+      t.snapshot(
+        cleanObject(afterRevert),
+        'should remove assistant message after revert'
+      );
+    }
   }
 });
 
diff --git a/packages/backend/server/src/__tests__/utils/copilot.ts b/packages/backend/server/src/__tests__/utils/copilot.ts
index f1ad92805..8703af56a 100644
--- a/packages/backend/server/src/__tests__/utils/copilot.ts
+++ b/packages/backend/server/src/__tests__/utils/copilot.ts
@@ -444,9 +444,12 @@ export async function chatWithText(
   app: TestingApp,
   sessionId: string,
   messageId?: string,
-  prefix = ''
+  prefix = '',
+  retry?: boolean
 ): Promise<string> {
-  const query = messageId ? `?messageId=${messageId}` : '';
+  const query = messageId
+    ? `?messageId=${messageId}` + (retry ? '&retry=true' : '')
+    : '';
   const res = await app
     .GET(`/api/copilot/chat/${sessionId}${prefix}${query}`)
     .expect(200);
diff --git a/packages/backend/server/src/plugins/copilot/controller.ts b/packages/backend/server/src/plugins/copilot/controller.ts
index afec7bf2f..9d6540403 100644
--- a/packages/backend/server/src/plugins/copilot/controller.ts
+++ b/packages/backend/server/src/plugins/copilot/controller.ts
@@ -137,20 +137,23 @@ export class CopilotController implements BeforeApplicationShutdown {
 
   private async appendSessionMessage(
     sessionId: string,
-    messageId?: string
+    messageId?: string,
+    retry = false
   ): Promise<ChatSession> {
     const session = await this.chatSession.get(sessionId);
     if (!session) {
       throw new CopilotSessionNotFound();
     }
 
+    if (!messageId || retry) {
+      // revert the latest message generated by the assistant
+      // if messageId is provided, we will also revert latest user message
+      await this.chatSession.revertLatestMessage(sessionId, !messageId);
+      session.revertLatestMessage(!messageId);
+    }
+
     if (messageId) {
       await session.pushByMessageId(messageId);
-    } else {
-      // revert the latest message generated by the assistant
-      // if messageId is not provided, then we can retry the action
-      await this.chatSession.revertLatestMessage(sessionId);
-      session.revertLatestMessage();
     }
 
     return session;
@@ -160,8 +163,12 @@ export class CopilotController implements BeforeApplicationShutdown {
     const messageId = Array.isArray(params.messageId)
       ? params.messageId[0]
       : params.messageId;
+    const retry = Array.isArray(params.retry)
+      ? Boolean(params.retry[0])
+      : Boolean(params.retry);
     delete params.messageId;
-    return { messageId, params };
+    delete params.retry;
+    return { messageId, retry, params };
   }
 
   private getSignal(req: Request) {
@@ -202,7 +209,7 @@ export class CopilotController implements BeforeApplicationShutdown {
     @Param('sessionId') sessionId: string,
     @Query() params: Record<string, string | string[]>
   ): Promise<string> {
-    const { messageId } = this.prepareParams(params);
+    const { messageId, retry } = this.prepareParams(params);
 
     const provider = await this.chooseTextProvider(
       user.id,
@@ -210,7 +217,11 @@ export class CopilotController implements BeforeApplicationShutdown {
       messageId
     );
 
-    const session = await this.appendSessionMessage(sessionId, messageId);
+    const session = await this.appendSessionMessage(
+      sessionId,
+      messageId,
+      retry
+    );
     try {
       metrics.ai.counter('chat_calls').add(1, { model: session.model });
       const content = await provider.generateText(
@@ -248,7 +259,7 @@ export class CopilotController implements BeforeApplicationShutdown {
     const info: any = { sessionId, params, throwInStream: false };
 
     try {
-      const { messageId } = this.prepareParams(params);
+      const { messageId, retry } = this.prepareParams(params);
 
       const provider = await this.chooseTextProvider(
         user.id,
@@ -256,7 +267,11 @@ export class CopilotController implements BeforeApplicationShutdown {
         messageId
       );
 
-      const session = await this.appendSessionMessage(sessionId, messageId);
+      const session = await this.appendSessionMessage(
+        sessionId,
+        messageId,
+        retry
+      );
       info.model = session.model;
 
       metrics.ai.counter('chat_stream_calls').add(1, { model: session.model });
diff --git a/packages/backend/server/src/plugins/copilot/session.ts b/packages/backend/server/src/plugins/copilot/session.ts
index 3d18f82bf..79837d7fc 100644
--- a/packages/backend/server/src/plugins/copilot/session.ts
+++ b/packages/backend/server/src/plugins/copilot/session.ts
@@ -75,10 +75,11 @@ export class ChatSession implements AsyncDisposable {
     this.stashMessageCount += 1;
   }
 
-  revertLatestMessage() {
+  revertLatestMessage(removeLatestUserMessage: boolean) {
     const messages = this.state.messages;
     messages.splice(
-      messages.findLastIndex(({ role }) => role === AiPromptRole.user) + 1
+      messages.findLastIndex(({ role }) => role === AiPromptRole.user) +
+        (removeLatestUserMessage ? 0 : 1)
     );
   }
 
@@ -341,7 +342,10 @@ export class ChatSessionService {
 
   // revert the latest messages not generate by user
   // after revert, we can retry the action
-  async revertLatestMessage(sessionId: string) {
+  async revertLatestMessage(
+    sessionId: string,
+    removeLatestUserMessage: boolean
+  ) {
     await this.db.$transaction(async tx => {
       const id = await tx.aiSession
         .findUnique({
@@ -361,7 +365,8 @@ export class ChatSessionService {
         .then(roles =>
           roles
             .slice(
-              roles.findLastIndex(({ role }) => role === AiPromptRole.user) + 1
+              roles.findLastIndex(({ role }) => role === AiPromptRole.user) +
+                (removeLatestUserMessage ? 0 : 1)
             )
             .map(({ id }) => id)
         );