diff --git a/apps/x/apps/renderer/src/components/sidebar-content.tsx b/apps/x/apps/renderer/src/components/sidebar-content.tsx
index 7e204781..9c50c334 100644
--- a/apps/x/apps/renderer/src/components/sidebar-content.tsx
+++ b/apps/x/apps/renderer/src/components/sidebar-content.tsx
@@ -156,6 +156,28 @@ const SERVICE_LABELS: Record<string, string> = {
   granola: "Syncing Granola",
   graph: "Updating knowledge",
   voice_memo: "Processing voice memo",
+  email_labeling: "Labeling emails",
+  note_tagging: "Tagging notes",
+  agent_notes: "Updating agent notes",
+}
+
+function summarizeServiceError(error: string): string {
+  const firstLine = error.split("\n").find((line) => line.trim().length > 0)
+  return firstLine?.trim() || error.trim()
+}
+
+function collectServiceErrors(events: ServiceEventType[]): Map<string, string> {
+  const errors = new Map<string, string>()
+  for (const event of events) {
+    if (event.type === "error") {
+      errors.set(event.service, summarizeServiceError(event.error))
+      continue
+    }
+    if (event.type === "run_complete" && event.outcome !== "error") {
+      errors.delete(event.service)
+    }
+  }
+  return errors
 }
 
 type TasksActions = {
@@ -227,6 +249,7 @@ function formatRunTime(ts: string): string {
 function SyncStatusBar() {
   const { state } = useSidebar()
   const [activeServices, setActiveServices] = useState<Map<string, string>>(new Map())
+  const [serviceErrors, setServiceErrors] = useState<Map<string, string>>(new Map())
   const [popoverOpen, setPopoverOpen] = useState(false)
   const [logEvents, setLogEvents] = useState<ServiceEventType[]>([])
   const [logLoading, setLogLoading] = useState(false)
@@ -260,11 +283,25 @@ function SyncStatusBar() {
           next.delete(nextEvent.runId)
           return next
         })
+        if (nextEvent.outcome !== 'error') {
+          setServiceErrors((prev) => {
+            if (!prev.has(nextEvent.service)) return prev
+            const next = new Map(prev)
+            next.delete(nextEvent.service)
+            return next
+          })
+        }
         const existingTimeout = runTimeoutsRef.current.get(nextEvent.runId)
         if (existingTimeout) {
           clearTimeout(existingTimeout)
           runTimeoutsRef.current.delete(nextEvent.runId)
         }
+      } else if (nextEvent.type === 'error') {
+        setServiceErrors((prev) => {
+          const next = new Map(prev)
+          next.set(nextEvent.service, summarizeServiceError(nextEvent.error))
+          return next
+        })
       }
     })
     return cleanup
@@ -298,10 +335,14 @@ function SyncStatusBar() {
             // skip malformed lines
           }
         }
+        setServiceErrors(collectServiceErrors(parsed))
         // Newest first, limit to 1000
         setLogEvents(parsed.reverse().slice(0, MAX_SYNC_EVENTS))
       } catch {
-        if (!cancelled) setLogEvents([])
+        if (!cancelled) {
+          setLogEvents([])
+          setServiceErrors(new Map())
+        }
       } finally {
         if (!cancelled) setLogLoading(false)
       }
@@ -312,12 +353,19 @@ function SyncStatusBar() {
 
   const isSyncing = activeServices.size > 0
   const isCollapsed = state === "collapsed"
+  const errorEntries = Array.from(serviceErrors.entries())
+  const primaryErrorService = errorEntries[0]?.[0] ?? null
+  const hasServiceErrors = errorEntries.length > 0
 
   // Build status label from active services
   const activeServiceNames = [...new Set(activeServices.values())]
   const statusLabel = isSyncing
     ? activeServiceNames.map((s) => SERVICE_LABELS[s] || s).join(", ")
-    : "All caught up"
+    : hasServiceErrors
+      ? errorEntries.length === 1
+        ? `${SERVICE_LABELS[primaryErrorService ?? ""] || primaryErrorService} failed`
+        : "Recent sync issues"
+      : "All caught up"
 
   return (
     <>
@@ -335,11 +383,16 @@ function SyncStatusBar() {
           <PopoverTrigger asChild>
             <button
               type="button"
-              className="flex w-full items-center justify-between rounded-md px-2 py-1 text-xs text-muted-foreground hover:bg-sidebar-accent"
+              className={cn(
+                "flex w-full items-center justify-between rounded-md px-2 py-1 text-xs hover:bg-sidebar-accent",
+                hasServiceErrors && !isSyncing ? "text-red-600 dark:text-red-400" : "text-muted-foreground",
+              )}
             >
               <span className="flex items-center gap-2 min-w-0">
                 {isSyncing ? (
                   <LoaderIcon className="h-3 w-3 shrink-0 animate-spin" />
+                ) : hasServiceErrors ? (
+                  <AlertTriangle className="h-3 w-3 shrink-0" />
                 ) : (
                   <span className="h-1.5 w-1.5 shrink-0 rounded-full bg-muted-foreground/60" />
                 )}
@@ -357,7 +410,7 @@ function SyncStatusBar() {
             <div className="p-3 border-b">
               <h4 className="font-semibold text-sm">Sync Activity</h4>
               <p className="text-xs text-muted-foreground mt-0.5">
-                {isSyncing ? statusLabel : "All services up to date"}
+                {isSyncing || hasServiceErrors ? statusLabel : "All services up to date"}
               </p>
             </div>
             <div className="max-h-80 overflow-y-auto p-2">
@@ -389,7 +442,17 @@ function SyncStatusBar() {
                           {SERVICE_LABELS[event.service]?.split(" ").slice(-1)[0] || event.service}
                         </span>
                       </span>
-                      <span className="leading-4 text-foreground/80">{event.message}</span>
+                      <div className="min-w-0 flex-1">
+                        <p className="leading-4 text-foreground/80">{event.message}</p>
+                        {event.type === 'error' && (
+                          <p
+                            className="truncate text-[11px] leading-4 text-red-600/90 dark:text-red-400/90"
+                            title={event.error}
+                          >
+                            {summarizeServiceError(event.error)}
+                          </p>
+                        )}
+                      </div>
                     </div>
                   ))}
                 </div>
diff --git a/apps/x/packages/core/src/agents/utils.ts b/apps/x/packages/core/src/agents/utils.ts
index bd4c84af..3e5f472e 100644
--- a/apps/x/packages/core/src/agents/utils.ts
+++ b/apps/x/packages/core/src/agents/utils.ts
@@ -1,6 +1,35 @@
 import { bus } from "../runs/bus.js";
 import { fetchRun } from "../runs/runs.js";
 
+type RunRecord = Awaited<ReturnType<typeof fetchRun>>;
+
+function extractRunErrors(run: RunRecord): string[] {
+    return run.log.flatMap((event) => event.type === "error" ? [event.error] : []);
+}
+
+export class RunFailedError extends Error {
+    readonly runId: string;
+    readonly errors: string[];
+
+    constructor(runId: string, errors: string[]) {
+        const firstError = errors.find(Boolean) ?? null;
+        super(firstError ? `Run ${runId} failed: ${firstError}` : `Run ${runId} failed`);
+        this.name = "RunFailedError";
+        this.runId = runId;
+        this.errors = errors;
+    }
+}
+
+export function getErrorDetails(error: unknown): string {
+    if (error instanceof RunFailedError) {
+        return error.errors.join("\n\n");
+    }
+    if (error instanceof Error) {
+        return error.message;
+    }
+    return String(error);
+}
+
 /**
  * Extract the assistant's final text response from a run's log.
  * @param runId 
@@ -28,13 +57,28 @@ export async function extractAgentResponse(runId: string): Promise<string | null
 /**
  * Wait for a run to complete by listening for run-processing-end event
  */
-export async function waitForRunCompletion(runId: string): Promise<void> {
-    return new Promise(async (resolve) => {
-        const unsubscribe = await bus.subscribe('*', async (event) => {
-            if (event.type === 'run-processing-end' && event.runId === runId) {
-                unsubscribe();
-                resolve();
-            }
-        });
+export async function waitForRunCompletion(
+    runId: string,
+    opts: { throwOnError?: boolean } = {},
+): Promise<RunRecord> {
+    return new Promise((resolve, reject) => {
+        void (async () => {
+            const unsubscribe = await bus.subscribe('*', async (event) => {
+                if (event.type === 'run-processing-end' && event.runId === runId) {
+                    unsubscribe();
+                    try {
+                        const run = await fetchRun(runId);
+                        const errors = extractRunErrors(run);
+                        if (opts.throwOnError && errors.length > 0) {
+                            reject(new RunFailedError(runId, errors));
+                            return;
+                        }
+                        resolve(run);
+                    } catch (error) {
+                        reject(error);
+                    }
+                }
+            });
+        })().catch(reject);
     });
-}
\ No newline at end of file
+}
diff --git a/apps/x/packages/core/src/knowledge/agent_notes.ts b/apps/x/packages/core/src/knowledge/agent_notes.ts
index 301c10a6..f1380c4a 100644
--- a/apps/x/packages/core/src/knowledge/agent_notes.ts
+++ b/apps/x/packages/core/src/knowledge/agent_notes.ts
@@ -4,7 +4,7 @@ import { google } from 'googleapis';
 import { WorkDir } from '../config/config.js';
 import { createRun, createMessage } from '../runs/runs.js';
 import { getKgModel } from '../models/defaults.js';
-import { waitForRunCompletion } from '../agents/utils.js';
+import { getErrorDetails, waitForRunCompletion } from '../agents/utils.js';
 import { serviceLogger } from '../services/service_logger.js';
 import { loadUserConfig, updateUserEmail } from '../config/user_config.js';
 import { GoogleClientFactory } from './google-client-factory.js';
@@ -288,7 +288,7 @@ async function processAgentNotes(): Promise<void> {
             subUseCase: 'agent_notes',
         });
         await createMessage(agentRun.id, message);
-        await waitForRunCompletion(agentRun.id);
+        await waitForRunCompletion(agentRun.id, { throwOnError: true });
 
         // Mark everything as processed
         for (const p of emailPaths) {
@@ -326,7 +326,16 @@ async function processAgentNotes(): Promise<void> {
             runId: serviceRun.runId,
             level: 'error',
             message: 'Error processing agent notes',
-            error: error instanceof Error ? error.message : String(error),
+            error: getErrorDetails(error),
+        });
+        await serviceLogger.log({
+            type: 'run_complete',
+            service: serviceRun.service,
+            runId: serviceRun.runId,
+            level: 'error',
+            message: 'Agent notes processing failed',
+            durationMs: Date.now() - serviceRun.startedAt,
+            outcome: 'error',
         });
     }
 }
diff --git a/apps/x/packages/core/src/knowledge/build_graph.ts b/apps/x/packages/core/src/knowledge/build_graph.ts
index d47413ca..10be1d14 100644
--- a/apps/x/packages/core/src/knowledge/build_graph.ts
+++ b/apps/x/packages/core/src/knowledge/build_graph.ts
@@ -3,7 +3,7 @@ import path from 'path';
 import { WorkDir } from '../config/config.js';
 import { createRun, createMessage } from '../runs/runs.js';
 import { bus } from '../runs/bus.js';
-import { waitForRunCompletion } from '../agents/utils.js';
+import { getErrorDetails, waitForRunCompletion } from '../agents/utils.js';
 import { serviceLogger, type ServiceRunContext } from '../services/service_logger.js';
 import {
     loadState,
@@ -312,8 +312,11 @@ async function createNotesFromBatch(
     await createMessage(run.id, message);
 
     // Wait for the run to complete
-    await waitForRunCompletion(run.id);
-    unsubscribe();
+    try {
+        await waitForRunCompletion(run.id, { throwOnError: true });
+    } finally {
+        unsubscribe();
+    }
 
     return { runId: run.id, notesCreated, notesModified };
 }
@@ -428,7 +431,7 @@ async function buildGraphWithFiles(
                     runId: run.runId,
                     level: 'error',
                     message: `Error processing batch ${batchNumber}`,
-                    error: error instanceof Error ? error.message : String(error),
+                    error: getErrorDetails(error),
                     context: { batchNumber },
                 });
             }
@@ -600,7 +603,7 @@ async function processVoiceMemosForKnowledge(): Promise<boolean> {
                 runId: run.runId,
                 level: 'error',
                 message: `Error processing voice memo batch ${batchNumber}`,
-                error: error instanceof Error ? error.message : String(error),
+                error: getErrorDetails(error),
                 context: { batchNumber },
             });
         }
diff --git a/apps/x/packages/core/src/knowledge/label_emails.ts b/apps/x/packages/core/src/knowledge/label_emails.ts
index 9ee57798..76ae579c 100644
--- a/apps/x/packages/core/src/knowledge/label_emails.ts
+++ b/apps/x/packages/core/src/knowledge/label_emails.ts
@@ -4,7 +4,7 @@ import { WorkDir } from '../config/config.js';
 import { createRun, createMessage } from '../runs/runs.js';
 import { getKgModel } from '../models/defaults.js';
 import { bus } from '../runs/bus.js';
-import { waitForRunCompletion } from '../agents/utils.js';
+import { getErrorDetails, waitForRunCompletion } from '../agents/utils.js';
 import { serviceLogger } from '../services/service_logger.js';
 import { limitEventItems } from './limit_event_items.js';
 import {
@@ -112,8 +112,11 @@ async function labelEmailBatch(
     });
 
     await createMessage(run.id, message);
-    await waitForRunCompletion(run.id);
-    unsubscribe();
+    try {
+        await waitForRunCompletion(run.id, { throwOnError: true });
+    } finally {
+        unsubscribe();
+    }
 
     return { runId: run.id, filesEdited };
 }
@@ -175,6 +178,7 @@ export async function processUnlabeledEmails(concurrency: number = DEFAULT_CONCU
     const totalBatches = batches.length;
     let totalEdited = 0;
     let hadError = false;
+    let failedBatches = 0;
 
     // Process batches with concurrency limit
     for (let i = 0; i < batches.length; i += concurrency) {
@@ -209,14 +213,16 @@ export async function processUnlabeledEmails(concurrency: number = DEFAULT_CONCU
                 return result.filesEdited.size;
             } catch (error) {
                 hadError = true;
+                failedBatches++;
+                const errorDetails = getErrorDetails(error);
                 console.error(`[EmailLabeling] Error processing batch ${batchNumber}:`, error);
                 await serviceLogger.log({
                     type: 'error',
                     service: run.service,
                     runId: run.runId,
                     level: 'error',
-                    message: `Error processing batch ${batchNumber}`,
-                    error: error instanceof Error ? error.message : String(error),
+                    message: `Email labeling batch ${batchNumber}/${totalBatches} failed`,
+                    error: errorDetails,
                     context: { batchNumber },
                 });
                 return 0;
@@ -238,12 +244,15 @@ export async function processUnlabeledEmails(concurrency: number = DEFAULT_CONCU
         service: run.service,
         runId: run.runId,
         level: hadError ? 'error' : 'info',
-        message: `Email labeling complete: ${totalEdited} files labeled`,
+        message: hadError
+            ? `Email labeling finished with errors: ${totalEdited} files labeled`
+            : `Email labeling complete: ${totalEdited} files labeled`,
         durationMs: Date.now() - run.startedAt,
         outcome: hadError ? 'error' : 'ok',
         summary: {
             totalEmails: unlabeled.length,
             filesLabeled: totalEdited,
+            failedBatches,
         },
     });
 
diff --git a/apps/x/packages/core/src/knowledge/tag_notes.ts b/apps/x/packages/core/src/knowledge/tag_notes.ts
index 7a888725..c1c45ae6 100644
--- a/apps/x/packages/core/src/knowledge/tag_notes.ts
+++ b/apps/x/packages/core/src/knowledge/tag_notes.ts
@@ -4,7 +4,7 @@ import { WorkDir } from '../config/config.js';
 import { createRun, createMessage } from '../runs/runs.js';
 import { getKgModel } from '../models/defaults.js';
 import { bus } from '../runs/bus.js';
-import { waitForRunCompletion } from '../agents/utils.js';
+import { getErrorDetails, waitForRunCompletion } from '../agents/utils.js';
 import { serviceLogger } from '../services/service_logger.js';
 import { limitEventItems } from './limit_event_items.js';
 import {
@@ -125,8 +125,11 @@ async function tagNoteBatch(
     });
 
     await createMessage(run.id, message);
-    await waitForRunCompletion(run.id);
-    unsubscribe();
+    try {
+        await waitForRunCompletion(run.id, { throwOnError: true });
+    } finally {
+        unsubscribe();
+    }
 
     return { runId: run.id, filesEdited };
 }
@@ -169,6 +172,7 @@ export async function processUntaggedNotes(): Promise<void> {
     const totalBatches = Math.ceil(untagged.length / BATCH_SIZE);
     let totalEdited = 0;
     let hadError = false;
+    let failedBatches = 0;
 
     for (let i = 0; i < untagged.length; i += BATCH_SIZE) {
         const batchPaths = untagged.slice(i, i + BATCH_SIZE);
@@ -217,14 +221,16 @@ export async function processUntaggedNotes(): Promise<void> {
             console.log(`[NoteTagging] Batch ${batchNumber}/${totalBatches} complete, ${result.filesEdited.size} files tagged`);
         } catch (error) {
             hadError = true;
+            failedBatches++;
+            const errorDetails = getErrorDetails(error);
             console.error(`[NoteTagging] Error processing batch ${batchNumber}:`, error);
             await serviceLogger.log({
                 type: 'error',
                 service: run.service,
                 runId: run.runId,
                 level: 'error',
-                message: `Error processing batch ${batchNumber}`,
-                error: error instanceof Error ? error.message : String(error),
+                message: `Note tagging batch ${batchNumber}/${totalBatches} failed`,
+                error: errorDetails,
                 context: { batchNumber },
             });
         }
@@ -238,12 +244,15 @@ export async function processUntaggedNotes(): Promise<void> {
         service: run.service,
         runId: run.runId,
         level: hadError ? 'error' : 'info',
-        message: `Note tagging complete: ${totalEdited} notes tagged`,
+        message: hadError
+            ? `Note tagging finished with errors: ${totalEdited} notes tagged`
+            : `Note tagging complete: ${totalEdited} notes tagged`,
         durationMs: Date.now() - run.startedAt,
         outcome: hadError ? 'error' : 'ok',
         summary: {
             totalNotes: untagged.length,
             notesTagged: totalEdited,
+            failedBatches,
         },
     });