diff --git a/packages/backend/server/src/plugins/copilot/context/job.ts b/packages/backend/server/src/plugins/copilot/context/job.ts
index a44b7cc69f..1b71eaa8bf 100644
--- a/packages/backend/server/src/plugins/copilot/context/job.ts
+++ b/packages/backend/server/src/plugins/copilot/context/job.ts
@@ -73,11 +73,18 @@ export class CopilotContextDocJob {
   }
 
   @OnEvent('workspace.doc.embedding')
-  async addDocEmbeddingQueue(docs: Events['workspace.doc.embedding']) {
+  async addDocEmbeddingQueue(
+    docs: Events['workspace.doc.embedding'],
+    contextId?: string
+  ) {
     if (!this.supportEmbedding) return;
 
     for (const { workspaceId, docId } of docs) {
-      await this.queue.add('doc.embedPendingDocs', { workspaceId, docId });
+      await this.queue.add('doc.embedPendingDocs', {
+        contextId,
+        workspaceId,
+        docId,
+      });
     }
   }
 
@@ -130,23 +137,24 @@ export class CopilotContextDocJob {
         fileId,
         chunkSize: total,
       });
-    } catch (e: any) {
-      const error = mapAnyError(e);
-      error.log('CopilotJob', {
-        workspaceId,
-        fileId,
-      });
-
+    } catch (error: any) {
       this.event.emit('workspace.file.embed.failed', {
         contextId,
         fileId,
-        error: e.toString(),
+        error: mapAnyError(error).message,
       });
+
+      // passthrough error to job queue
+      throw error;
     }
   }
 
   @OnJob('doc.embedPendingDocs')
-  async embedPendingDocs({ workspaceId, docId }: Jobs['doc.embedPendingDocs']) {
+  async embedPendingDocs({
+    contextId,
+    workspaceId,
+    docId,
+  }: Jobs['doc.embedPendingDocs']) {
     if (!this.supportEmbedding) return;
 
     try {
@@ -165,11 +173,16 @@ export class CopilotContextDocJob {
           );
         }
       }
-    } catch (e: any) {
-      this.logger.error(
-        `Failed to embed pending doc: ${workspaceId}::${docId}`,
-        e
-      );
+    } catch (error: any) {
+      if (contextId) {
+        this.event.emit('workspace.doc.embed.failed', {
+          contextId,
+          docId,
+        });
+      }
+
+      // passthrough error to job queue
+      throw error;
     }
   }
 }
diff --git a/packages/backend/server/src/plugins/copilot/context/resolver.ts b/packages/backend/server/src/plugins/copilot/context/resolver.ts
index e12da3a5ea..7117cb483e 100644
--- a/packages/backend/server/src/plugins/copilot/context/resolver.ts
+++ b/packages/backend/server/src/plugins/copilot/context/resolver.ts
@@ -464,7 +464,8 @@ export class CopilotContextResolver {
           options.docs.map(docId => ({
             workspaceId: session.workspaceId,
             docId,
-          }))
+          })),
+          session.id
         );
       }
 
@@ -523,12 +524,10 @@ export class CopilotContextResolver {
     try {
       const record = await session.addDocRecord(options.docId);
 
-      await this.jobs.addDocEmbeddingQueue([
-        {
-          workspaceId: session.workspaceId,
-          docId: options.docId,
-        },
-      ]);
+      await this.jobs.addDocEmbeddingQueue(
+        [{ workspaceId: session.workspaceId, docId: options.docId }],
+        session.id
+      );
 
       return { ...record, status: record.status || null };
     } catch (e: any) {
diff --git a/packages/backend/server/src/plugins/copilot/context/service.ts b/packages/backend/server/src/plugins/copilot/context/service.ts
index b9b5bf2307..f666733163 100644
--- a/packages/backend/server/src/plugins/copilot/context/service.ts
+++ b/packages/backend/server/src/plugins/copilot/context/service.ts
@@ -11,6 +11,7 @@ import {
 import {
   ContextConfig,
   ContextConfigSchema,
+  ContextDoc,
   ContextEmbedStatus,
   ContextFile,
   Models,
@@ -148,6 +149,18 @@ export class CopilotContextService implements OnApplicationBootstrap {
     return null;
   }
 
+  @OnEvent('workspace.doc.embed.failed')
+  async onDocEmbedFailed({
+    contextId,
+    docId,
+  }: Events['workspace.doc.embed.failed']) {
+    const context = await this.get(contextId);
+    await context.saveDocRecord(docId, doc => ({
+      ...(doc as ContextDoc),
+      status: ContextEmbedStatus.failed,
+    }));
+  }
+
   @OnEvent('workspace.file.embed.finished')
   async onFileEmbedFinish({
     contextId,
diff --git a/packages/backend/server/src/plugins/copilot/context/session.ts b/packages/backend/server/src/plugins/copilot/context/session.ts
index 39de23cef4..34047df568 100644
--- a/packages/backend/server/src/plugins/copilot/context/session.ts
+++ b/packages/backend/server/src/plugins/copilot/context/session.ts
@@ -217,6 +217,23 @@ export class ContextSession implements AsyncDisposable {
     );
   }
 
+  async saveDocRecord(
+    docId: string,
+    cb: (
+      record: Pick<ContextDoc, 'id' | 'status'> &
+        Partial<Omit<ContextDoc, 'id' | 'status'>>
+    ) => ContextDoc
+  ) {
+    const docs = [this.config.docs, ...this.config.categories.map(c => c.docs)]
+      .flat()
+      .filter(d => d.id === docId);
+    for (const doc of docs) {
+      Object.assign(doc, cb({ ...doc }));
+    }
+
+    await this.save();
+  }
+
   async saveFileRecord(
     fileId: string,
     cb: (
diff --git a/packages/backend/server/src/plugins/copilot/context/types.ts b/packages/backend/server/src/plugins/copilot/context/types.ts
index fbd6a6a50e..ac089b9959 100644
--- a/packages/backend/server/src/plugins/copilot/context/types.ts
+++ b/packages/backend/server/src/plugins/copilot/context/types.ts
@@ -10,11 +10,18 @@ declare global {
       workspaceId: string;
       docId: string;
     }>;
+
+    'workspace.doc.embed.failed': {
+      contextId: string;
+      docId: string;
+    };
+
     'workspace.file.embed.finished': {
       contextId: string;
       fileId: string;
       chunkSize: number;
     };
+
     'workspace.file.embed.failed': {
       contextId: string;
       fileId: string;
@@ -23,6 +30,7 @@ declare global {
   }
   interface Jobs {
     'doc.embedPendingDocs': {
+      contextId?: string;
       workspaceId: string;
       docId: string;
     };