Scheduled tasks re-prompt for tool permissions on automatic/cron fires despite prior manual approval

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?

Summary: Scheduled tasks (Routines) do not inherit tool-permission approvals when triggered automatically by their cron schedule, even after the same task has been run and fully approved manually. Every automatic fire re-prompts for permissions with no one present to answer, causing the run to hang indefinitely.

Environment:

OS: Windows 11 Pro (build 10.0.26100)
Claude Code version: [check via Help/About and fill in]
Affected feature: Scheduled Tasks / Routines (local execution)
Steps to reproduce:

Create a scheduled task that calls at least one tool requiring permission approval (e.g., an MCP connector action, or a local file write).
Run it manually and approve every prompt — including using "Run now," which the in-app guidance describes as pre-approving the task for future runs.
Wait for the task's next automatic/cron-triggered fire.
Observe: the automatic run hits fresh permission prompts for the same tool calls already approved in step 2, with no one available to answer them, and the run hangs.
Expected behavior: An automatic fire of a task that has already been approved (via manual run or "Run now") should not re-prompt for the same tool permissions.

Actual behavior: Every automatic fire re-prompts, regardless of prior approval. Confirmed across multiple independent scheduled tasks and tool/connector combinations over a 3+ week period, with a 100% failure-to-run-clean rate on automatic fires specifically (manual fires are unaffected).

Already attempted, did not resolve it:

Approving via "Run now" (per documented behavior, should persist — did not).
Setting permissions.defaultMode: bypassPermissions at the project level — a tool already on the allow-list still prompted during an automatic fire.
Additional notes: This appears specific to the automatic/cron trigger path, not to permissions generally — manual runs of the identical task, with identical tool calls, complete cleanly once approved.

What Should Happen?

An automatic fire of a task that has already been approved (via a manual run or 'Run now') should not re-prompt for the same tool permissions — it should run cleanly using the previously-granted approvals, the same way the manual run did

Error Messages/Logs

No error is thrown — the run doesn't fail, it hangs indefinitely on an unanswered tool-permission prompt (the same approval dialog seen in an interactive session), with no one present to respond. If Anthropic has access to server-side logs for the task, they'd show the last activity timestamp stalled at the point of the tool call, with no completion or error recorded after it.

Steps to Reproduce

1. Create a scheduled task (Routine) that calls at least one tool requiring permission approval — any MCP connector action or local file write qualifies.
2. Run it manually and approve every prompt, including via "Run now" — the in-app guidance states this pre-approves the task for future runs.
3. Wait for the task's next automatic/cron-triggered fire.
4. Observe: the automatic run hits fresh permission prompts for the same tool calls already approved in step 2, with no one present to answer them — the run hangs indefinitely instead of completing.
5. Reproduced across multiple independent scheduled tasks with different tool/connector combinations over a 3+ week period — not specific to one task's content.

Claude Model

Sonnet (default)

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

version 1.22209.0

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

_No response_