[ChatGPT Work] Unsent external actions can silently fall out of a task

Problem

ChatGPT Work can prepare an external action such as an email, complete a neighboring action, and then leave the intended action unsent without a persistent warning or unresolved-action indicator.

The conversation may contain statements that the message remains unsent, but once the workflow moves on, nothing durable keeps that fact visible. The overall interaction can therefore leave the user believing the requested work was completed.

The reporting user estimates that similar “I thought ChatGPT had done it, but days later discovered it had not” incidents have occurred roughly 50 times over several months.

Representative incident

1. Two related emails were prepared.
2. ChatGPT sent the first email.
3. The user instructed ChatGPT to proceed with the second.
4. Further changes were discussed for the second email.
5. The workflow ended without the second email being sent.
6. No persistent task-level warning showed that an expected outbound action remained incomplete.
7. Days later, the user had to reconcile ChatGPT task history, Gmail Drafts, Sent, recipients, and timestamps to establish that it had never gone out.

The report is anonymized; customer names, addresses, message content, and Gmail identifiers are omitted.

Why this is severe

For sales, legal, finance, and customer communication, “prepared” and “sent” are fundamentally different states. Silent incompletion causes missed commitments, delayed follow-ups, and loss of trust in ChatGPT as an operational tool.

Requested behavior

• Give every external action a persistent state: DRAFTED, AWAITING APPROVAL, SENDING, SENT, FAILED, or CANCELLED.
• Keep unresolved actions prominently pinned until completed or explicitly dismissed.
• Warn when a task ends or moves on while an expected outbound action remains unsent.
• Never use completion-like language without confirmation from the external service.
• After edits interrupt a send flow, show a durable NOT SENT banner.
• For completed actions, provide a receipt containing the destination, timestamp, provider identifier, and direct link.
• Surface stale drafts and incomplete actions when reopening a task.

Expected result

A user should never reasonably leave a ChatGPT Work task believing an external action was completed unless ChatGPT has a confirmed provider receipt. Any unfinished action should remain unmistakably visible.

Related issues

• #41137 requests visible indicators for unsent drafts.
• #41529 requests durable status and receipts for ambiguous external-action outcomes. This report covers a distinct failure mode: a known pending action quietly falling out of the workflow without a persistent unresolved-action signal.

No files or tests are named. Start by comparing this report with related issues #41137 and #41529, then trace how ChatGPT Work represents external actions across task transitions and provider confirmation. Done means pending actions remain visible, completion is backed by a provider receipt, and interrupted or stale actions produce a durable unresolved warning.