[BUG] Cloud scheduled Cowork task completes and generates final message but hangs indefinitely at "Sending notification" — push/email never delivered

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

A cloud scheduled task in Cowork (recurring daily briefing) reliably finishes all of its work — including generating the full final message that is meant to be delivered — but the run then hangs indefinitely on the delivery step, showing "Invio notifica in corso…" / "Sending notification" spinning forever. The push notification and email are never delivered. Meanwhile the run appears stuck in the sidebar under Scheduled with the spinner still active.

The workaround (and the diagnostic tell) is that simply opening the stuck session from the Scheduled sidebar unblocks it: within about a minute of opening it, the "Sending notification" step completes. So the work product is fine — it's purely the automated delivery/notification hand-off at the end of the session that stalls.

This is intermittent: same daily task, same prompt, same connectors. It hung on 2026-07-15, 2026-07-16 and 2026-07-20, but delivered normally on 2026-07-17, 2026-07-18 and 2026-07-19. Because the task runs remotely (cloud), this is independent of the local machine, the desktop app, or whether the computer is awake — it was observed entirely from the web UI on a machine that had nothing to do with the run.

Task details:

• Type: cloud scheduled Cowork task, cadence daily 08:30 Europe/Rome
• Connectors used by the task: Gmail (read) + web search
• Affected session id (one of the stuck runs): cse_01QRBnv5q4KNhfwJ3vVNsDFe
• The stuck runs left no visible error message — just the perpetual "Sending notification" spinner.

What Should Happen?

When a scheduled task finishes generating its final message, delivery should complete on its own — the push notification and email should be sent without the user having to open the session. If delivery genuinely fails, it should surface a visible error and retry automatically, rather than hanging indefinitely on "Sending notification" with no feedback and no timeout.

Error Messages/Logs

Steps to Reproduce

1. Create a recurring cloud scheduled task in Cowork (e.g. a daily briefing at a fixed time) whose prompt ends by producing a final message intended to be delivered as a push notification / email. In this case the task also uses the Gmail connector (read) plus web search.
2. Let it run automatically on its schedule without opening the session.
3. Observe some runs: the session does all the work and generates the complete final message, then the run stalls on "Invio notifica in corso…" / "Sending notification" and stays there indefinitely (observed 3+ hours). No push and no email are delivered.
4. Open the stuck session from the Scheduled sidebar → within ~1 minute the "Sending notification" step completes (i.e. opening it unblocks delivery).

Note: intermittent — with the identical task it failed to deliver on 2026-07-15, 07-16 and 07-20 but delivered normally on 07-17, 07-18 and 07-19.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

N/A — not Claude Code CLI. This is a cloud-hosted Cowork scheduled task run from claude.ai (web), which has no CLI version.

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

The task is otherwise healthy: it runs on schedule, reads Gmail, runs web searches, and produces a correct final briefing every time. The only failure is the automated notification/delivery hand-off at the very end of the session, which intermittently never completes. Related note: no delivery email for this task is present in the connected Gmail account for any of the past ~10 days (including days that delivered successfully), which may or may not be relevant to where notifications are being routed.