diff --git a/src/features/background-agent/manager.ts b/src/features/background-agent/manager.ts
index 0dea79cb..e7b14f49 100644
--- a/src/features/background-agent/manager.ts
+++ b/src/features/background-agent/manager.ts
@@ -556,6 +556,11 @@ cleanup(): void {
   }
 
 private async notifyParentSession(task: BackgroundTask): Promise<void> {
+    if (task.concurrencyKey) {
+      this.concurrencyManager.release(task.concurrencyKey)
+      task.concurrencyKey = undefined
+    }
+
     const duration = this.formatDuration(task.startedAt, task.completedAt)
 
     log("[background-agent] notifyParentSession called for task:", task.id)
@@ -636,13 +641,8 @@ Use \`background_output(task_id="${task.id}")\` to retrieve this result when rea
       log("[background-agent] Failed to send notification:", error)
     }
 
-    // Cleanup after retention period
     const taskId = task.id
     setTimeout(() => {
-      if (task.concurrencyKey) {
-        this.concurrencyManager.release(task.concurrencyKey)
-        task.concurrencyKey = undefined
-      }
       this.clearNotificationsForTask(taskId)
       this.tasks.delete(taskId)
       log("[background-agent] Removed completed task from memory:", taskId)
diff --git a/src/tools/call-omo-agent/tools.ts b/src/tools/call-omo-agent/tools.ts
index c9ea3814..1c6e21b9 100644
--- a/src/tools/call-omo-agent/tools.ts
+++ b/src/tools/call-omo-agent/tools.ts
@@ -191,7 +191,58 @@ async function executeSync(
     return `Error: Failed to send prompt: ${errorMessage}\n\n<task_metadata>\nsession_id: ${sessionID}\n</task_metadata>`
   }
 
-  log(`[call_omo_agent] Prompt sent, fetching messages...`)
+  log(`[call_omo_agent] Prompt sent, polling for completion...`)
+
+  // Poll for session completion
+  const POLL_INTERVAL_MS = 500
+  const MAX_POLL_TIME_MS = 5 * 60 * 1000 // 5 minutes max
+  const pollStart = Date.now()
+  let lastMsgCount = 0
+  let stablePolls = 0
+  const STABILITY_REQUIRED = 3
+
+  while (Date.now() - pollStart < MAX_POLL_TIME_MS) {
+    // Check if aborted
+    if (toolContext.abort?.aborted) {
+      log(`[call_omo_agent] Aborted by user`)
+      return `Task aborted.\n\n<task_metadata>\nsession_id: ${sessionID}\n</task_metadata>`
+    }
+
+    await new Promise(resolve => setTimeout(resolve, POLL_INTERVAL_MS))
+
+    // Check session status
+    const statusResult = await ctx.client.session.status()
+    const allStatuses = (statusResult.data ?? {}) as Record<string, { type: string }>
+    const sessionStatus = allStatuses[sessionID]
+
+    // If session is actively running, reset stability counter
+    if (sessionStatus && sessionStatus.type !== "idle") {
+      stablePolls = 0
+      lastMsgCount = 0
+      continue
+    }
+
+    // Session is idle - check message stability
+    const messagesCheck = await ctx.client.session.messages({ path: { id: sessionID } })
+    const msgs = ((messagesCheck as { data?: unknown }).data ?? messagesCheck) as Array<unknown>
+    const currentMsgCount = msgs.length
+
+    if (currentMsgCount > 0 && currentMsgCount === lastMsgCount) {
+      stablePolls++
+      if (stablePolls >= STABILITY_REQUIRED) {
+        log(`[call_omo_agent] Session complete, ${currentMsgCount} messages`)
+        break
+      }
+    } else {
+      stablePolls = 0
+      lastMsgCount = currentMsgCount
+    }
+  }
+
+  if (Date.now() - pollStart >= MAX_POLL_TIME_MS) {
+    log(`[call_omo_agent] Timeout reached`)
+    return `Error: Agent task timed out after 5 minutes.\n\n<task_metadata>\nsession_id: ${sessionID}\n</task_metadata>`
+  }
 
   const messagesResult = await ctx.client.session.messages({
     path: { id: sessionID },
diff --git a/src/tools/sisyphus-task/tools.ts b/src/tools/sisyphus-task/tools.ts
index 58fc9e9b..060f0421 100644
--- a/src/tools/sisyphus-task/tools.ts
+++ b/src/tools/sisyphus-task/tools.ts
@@ -471,36 +471,55 @@ System notifies on completion. Use \`background_output\` with task_id="${task.id
         const pollStart = Date.now()
         let lastMsgCount = 0
         let stablePolls = 0
+        let pollCount = 0
+
+        log("[sisyphus_task] Starting poll loop", { sessionID, agentToUse })
 
         while (Date.now() - pollStart < MAX_POLL_TIME_MS) {
+          if (ctx.abort?.aborted) {
+            log("[sisyphus_task] Aborted by user", { sessionID })
+            if (toastManager && taskId) toastManager.removeTask(taskId)
+            return `Task aborted.\n\nSession ID: ${sessionID}`
+          }
+
           await new Promise(resolve => setTimeout(resolve, POLL_INTERVAL_MS))
+          pollCount++
 
           const statusResult = await client.session.status()
           const allStatuses = (statusResult.data ?? {}) as Record<string, { type: string }>
           const sessionStatus = allStatuses[sessionID]
 
-          // If session is actively running, reset stability
+          if (pollCount % 10 === 0) {
+            log("[sisyphus_task] Poll status", {
+              sessionID,
+              pollCount,
+              elapsed: Math.floor((Date.now() - pollStart) / 1000) + "s",
+              sessionStatus: sessionStatus?.type ?? "not_in_status",
+              stablePolls,
+              lastMsgCount,
+            })
+          }
+
           if (sessionStatus && sessionStatus.type !== "idle") {
             stablePolls = 0
             lastMsgCount = 0
             continue
           }
 
-          // Session is idle or not in status - check message stability
           const elapsed = Date.now() - pollStart
           if (elapsed < MIN_STABILITY_TIME_MS) {
-            continue  // Don't accept completion too early
+            continue
           }
 
-          // Get current message count
           const messagesCheck = await client.session.messages({ path: { id: sessionID } })
           const msgs = ((messagesCheck as { data?: unknown }).data ?? messagesCheck) as Array<unknown>
           const currentMsgCount = msgs.length
 
-          if (currentMsgCount > 0 && currentMsgCount === lastMsgCount) {
+          if (currentMsgCount === lastMsgCount) {
             stablePolls++
             if (stablePolls >= STABILITY_POLLS_REQUIRED) {
-              break  // Messages stable for 3 polls - task complete
+              log("[sisyphus_task] Poll complete - messages stable", { sessionID, pollCount, currentMsgCount })
+              break
             }
           } else {
             stablePolls = 0
@@ -508,6 +527,10 @@ System notifies on completion. Use \`background_output\` with task_id="${task.id
           }
         }
 
+        if (Date.now() - pollStart >= MAX_POLL_TIME_MS) {
+          log("[sisyphus_task] Poll timeout reached", { sessionID, pollCount, lastMsgCount, stablePolls })
+        }
+
         const messagesResult = await client.session.messages({
           path: { id: sessionID },
         })