diff --git a/packages/frontend/core/src/blocksuite/ai/components/ai-chat-content/ai-chat-content.ts b/packages/frontend/core/src/blocksuite/ai/components/ai-chat-content/ai-chat-content.ts
index edb86fb46..812b4596d 100644
--- a/packages/frontend/core/src/blocksuite/ai/components/ai-chat-content/ai-chat-content.ts
+++ b/packages/frontend/core/src/blocksuite/ai/components/ai-chat-content/ai-chat-content.ts
@@ -391,6 +391,7 @@ export class AIChatContent extends SignalWatcher(
               })
               .catch(console.error);
           }
+          AIProvider.slots.requestOpenWithChat.next(null);
         }
       )
     );
diff --git a/packages/frontend/core/src/blocksuite/ai/components/ai-chat-input/ai-chat-input.ts b/packages/frontend/core/src/blocksuite/ai/components/ai-chat-input/ai-chat-input.ts
index 2093c0eec..948b21e3a 100644
--- a/packages/frontend/core/src/blocksuite/ai/components/ai-chat-input/ai-chat-input.ts
+++ b/packages/frontend/core/src/blocksuite/ai/components/ai-chat-input/ai-chat-input.ts
@@ -405,6 +405,7 @@ export class AIChatInput extends SignalWatcher(
               this.send(input).catch(console.error);
             }, 0);
           }
+          AIProvider.slots.requestSendWithChat.next(null);
         }
       )
     );
diff --git a/packages/frontend/core/src/blocksuite/ai/components/ai-chat-toolbar/ai-chat-toolbar.ts b/packages/frontend/core/src/blocksuite/ai/components/ai-chat-toolbar/ai-chat-toolbar.ts
index c6a5ff8aa..26e21265e 100644
--- a/packages/frontend/core/src/blocksuite/ai/components/ai-chat-toolbar/ai-chat-toolbar.ts
+++ b/packages/frontend/core/src/blocksuite/ai/components/ai-chat-toolbar/ai-chat-toolbar.ts
@@ -92,14 +92,20 @@ export class AIChatToolbar extends WithDisposable(ShadowlessElement) {
     const pinned = this.session?.pinned;
     return html`
       <div class="ai-chat-toolbar">
-        <div class="chat-toolbar-icon" @click=${this.onPlusClick}>
+        <div
+          class="chat-toolbar-icon"
+          @click=${this.onPlusClick}
+          data-testid="ai-panel-new-chat"
+        >
           ${PlusIcon()}
           <affine-tooltip>New Chat</affine-tooltip>
         </div>
         <div
           class="chat-toolbar-icon"
           @click=${this.onPinClick}
+          data-pinned=${!!pinned}
           data-disabled=${this.isGenerating}
+          data-testid="ai-panel-pin-chat"
         >
           ${pinned ? PinedIcon() : PinIcon()}
           <affine-tooltip>
diff --git a/tests/affine-cloud-copilot/e2e/basic/chat.spec.ts b/tests/affine-cloud-copilot/e2e/basic/chat.spec.ts
index 637f98648..afb0dae44 100644
--- a/tests/affine-cloud-copilot/e2e/basic/chat.spec.ts
+++ b/tests/affine-cloud-copilot/e2e/basic/chat.spec.ts
@@ -450,4 +450,89 @@ test.describe('AIBasic/Chat', () => {
       },
     ]);
   });
+
+  test('should support create a new chat after ask ai', async ({
+    loggedInPage: page,
+    utils,
+  }) => {
+    await utils.chatPanel.closeChatPanel(page);
+    await utils.editor.askAIWithText(
+      page,
+      'AFFiNE is an open source all in one workspace.'
+    );
+    await page.keyboard.type('Translate to chinese.');
+
+    const sendButton = await page.getByTestId('ai-panel-input-send');
+    await expect(sendButton).toHaveAttribute('data-active', 'true');
+    await sendButton.click();
+
+    await expect(page.getByTestId('sidebar-tab-content-chat')).toBeVisible();
+    await utils.chatPanel.waitForHistory(page, [
+      {
+        role: 'user',
+        content:
+          'AFFiNE is an open source all in one workspace.\nTranslate to chinese.',
+      },
+      {
+        role: 'assistant',
+        status: 'success',
+      },
+    ]);
+
+    await page.getByTestId('ai-panel-new-chat').click();
+    await page.waitForTimeout(1000);
+    await utils.chatPanel.expectToHaveHistory(page, []);
+  });
+
+  test('should support pin chat', async ({ loggedInPage: page, utils }) => {
+    await utils.chatPanel.openChatPanel(page);
+    await utils.chatPanel.makeChat(
+      page,
+      'Hello, how can you help me? Answer in 50 words.'
+    );
+
+    await utils.chatPanel.waitForHistory(page, [
+      {
+        role: 'user',
+        content: 'Hello, how can you help me? Answer in 50 words.',
+      },
+      {
+        role: 'assistant',
+        status: 'success',
+      },
+    ]);
+
+    // pinned
+    await expect(page.getByTestId('ai-panel-pin-chat')).toHaveAttribute(
+      'data-pinned',
+      'false'
+    );
+    await page.getByTestId('ai-panel-pin-chat').click();
+    await expect(page.getByTestId('ai-panel-pin-chat')).toHaveAttribute(
+      'data-pinned',
+      'true'
+    );
+
+    // create new doc
+    await utils.editor.createDoc(page, 'Doc 1', 'doc1');
+    await utils.chatPanel.expectToHaveHistory(page, [
+      {
+        role: 'user',
+        content: 'Hello, how can you help me? Answer in 50 words.',
+      },
+      {
+        role: 'assistant',
+        status: 'idle',
+      },
+    ]);
+    await page.getByTestId('ai-panel-pin-chat').click();
+
+    // unpinned
+    await expect(page.getByTestId('ai-panel-pin-chat')).toHaveAttribute(
+      'data-pinned',
+      'false'
+    );
+    await utils.editor.createDoc(page, 'Doc 2', 'doc2');
+    await utils.chatPanel.expectToHaveHistory(page, []);
+  });
 });