diff --git a/packages/frontend/core/src/blocksuite/ai/chat-panel/chat-panel-chips.ts b/packages/frontend/core/src/blocksuite/ai/chat-panel/chat-panel-chips.ts
index 1459786cb..8f22650f6 100644
--- a/packages/frontend/core/src/blocksuite/ai/chat-panel/chat-panel-chips.ts
+++ b/packages/frontend/core/src/blocksuite/ai/chat-panel/chat-panel-chips.ts
@@ -361,10 +361,6 @@ export class ChatPanelChips extends SignalWatcher(
   };
 
   private readonly _addToContext = async (chip: ChatChip) => {
-    const contextId = await this.getContextId();
-    if (!contextId || !AIProvider.context) {
-      return;
-    }
     if (isDocChip(chip)) {
       return await this._addDocToContext(chip);
     }
@@ -381,11 +377,11 @@ export class ChatPanelChips extends SignalWatcher(
   };
 
   private readonly _addDocToContext = async (chip: DocChip) => {
-    const contextId = await this.getContextId();
-    if (!contextId || !AIProvider.context) {
-      return;
-    }
     try {
+      const contextId = await this.getContextId();
+      if (!contextId || !AIProvider.context) {
+        throw new Error('Context not found');
+      }
       await AIProvider.context.addContextDoc({
         contextId,
         docId: chip.docId,
@@ -399,11 +395,11 @@ export class ChatPanelChips extends SignalWatcher(
   };
 
   private readonly _addFileToContext = async (chip: FileChip) => {
-    const contextId = await this.getContextId();
-    if (!contextId || !AIProvider.context) {
-      return;
-    }
     try {
+      const contextId = await this.getContextId();
+      if (!contextId || !AIProvider.context) {
+        throw new Error('Context not found');
+      }
       const blobId = await this.host.doc.blobSync.set(chip.file);
       const contextFile = await AIProvider.context.addContextFile(chip.file, {
         contextId,
@@ -423,11 +419,11 @@ export class ChatPanelChips extends SignalWatcher(
   };
 
   private readonly _addTagToContext = async (chip: TagChip) => {
-    const contextId = await this.getContextId();
-    if (!contextId || !AIProvider.context) {
-      return;
-    }
     try {
+      const contextId = await this.getContextId();
+      if (!contextId || !AIProvider.context) {
+        throw new Error('Context not found');
+      }
       // TODO: server side docIds calculation
       const docIds = this.docDisplayConfig.getTagPageIds(chip.tagId);
       await AIProvider.context.addContextTag({
@@ -447,11 +443,11 @@ export class ChatPanelChips extends SignalWatcher(
   };
 
   private readonly _addCollectionToContext = async (chip: CollectionChip) => {
-    const contextId = await this.getContextId();
-    if (!contextId || !AIProvider.context) {
-      return;
-    }
     try {
+      const contextId = await this.getContextId();
+      if (!contextId || !AIProvider.context) {
+        throw new Error('Context not found');
+      }
       const collection = this._collections.value.find(
         collection => collection.id === chip.collectionId
       );
@@ -477,35 +473,39 @@ export class ChatPanelChips extends SignalWatcher(
   private readonly _removeFromContext = async (
     chip: ChatChip
   ): Promise<boolean> => {
-    const contextId = await this.getContextId();
-    if (!contextId || !AIProvider.context) {
-      return false;
+    try {
+      const contextId = await this.getContextId();
+      if (!contextId || !AIProvider.context) {
+        return true;
+      }
+      if (isDocChip(chip)) {
+        return await AIProvider.context.removeContextDoc({
+          contextId,
+          docId: chip.docId,
+        });
+      }
+      if (isFileChip(chip) && chip.fileId) {
+        return await AIProvider.context.removeContextFile({
+          contextId,
+          fileId: chip.fileId,
+        });
+      }
+      if (isTagChip(chip)) {
+        return await AIProvider.context.removeContextTag({
+          contextId,
+          tagId: chip.tagId,
+        });
+      }
+      if (isCollectionChip(chip)) {
+        return await AIProvider.context.removeContextCollection({
+          contextId,
+          collectionId: chip.collectionId,
+        });
+      }
+      return true;
+    } catch {
+      return true;
     }
-    if (isDocChip(chip)) {
-      return await AIProvider.context.removeContextDoc({
-        contextId,
-        docId: chip.docId,
-      });
-    }
-    if (isFileChip(chip) && chip.fileId) {
-      return await AIProvider.context.removeContextFile({
-        contextId,
-        fileId: chip.fileId,
-      });
-    }
-    if (isTagChip(chip)) {
-      return await AIProvider.context.removeContextTag({
-        contextId,
-        tagId: chip.tagId,
-      });
-    }
-    if (isCollectionChip(chip)) {
-      return await AIProvider.context.removeContextCollection({
-        contextId,
-        collectionId: chip.collectionId,
-      });
-    }
-    return true;
   };
 
   private readonly _checkTokenLimit = (
diff --git a/packages/frontend/core/src/blocksuite/ai/chat-panel/index.ts b/packages/frontend/core/src/blocksuite/ai/chat-panel/index.ts
index 94a3853e0..61886e31a 100644
--- a/packages/frontend/core/src/blocksuite/ai/chat-panel/index.ts
+++ b/packages/frontend/core/src/blocksuite/ai/chat-panel/index.ts
@@ -328,25 +328,32 @@ export class ChatPanel extends SignalWatcher(
   private readonly _cleanupHistories = async () => {
     const notification = this.host.std.getOptional(NotificationProvider);
     if (!notification) return;
-
-    if (
-      await notification.confirm({
-        title: 'Clear History',
-        message:
-          'Are you sure you want to clear all history? This action will permanently delete all content, including all chat logs and data, and cannot be undone.',
-        confirmText: 'Confirm',
-        cancelText: 'Cancel',
-      })
-    ) {
-      const actionIds = this.chatContextValue.items
-        .filter(item => 'sessionId' in item)
-        .map(item => item.sessionId);
-      await AIProvider.histories?.cleanup(this.doc.workspace.id, this.doc.id, [
-        ...(this._chatSessionId ? [this._chatSessionId] : []),
-        ...(actionIds || []),
-      ]);
-      notification.toast('History cleared');
-      await this._updateHistory();
+    try {
+      if (
+        await notification.confirm({
+          title: 'Clear History',
+          message:
+            'Are you sure you want to clear all history? This action will permanently delete all content, including all chat logs and data, and cannot be undone.',
+          confirmText: 'Confirm',
+          cancelText: 'Cancel',
+        })
+      ) {
+        const actionIds = this.chatContextValue.items
+          .filter(item => 'sessionId' in item)
+          .map(item => item.sessionId);
+        await AIProvider.histories?.cleanup(
+          this.doc.workspace.id,
+          this.doc.id,
+          [
+            ...(this._chatSessionId ? [this._chatSessionId] : []),
+            ...(actionIds || []),
+          ]
+        );
+        notification.toast('History cleared');
+        await this._updateHistory();
+      }
+    } catch {
+      notification.toast('Failed to clear history');
     }
   };