[BUG] "Allow for all scheduled runs" permission does not persist — re-prompts on every scheduled run
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?
Description:
I have a Cowork scheduled task (hourly Jira-email-to-Slack triage job) that calls the Gmail "Send email message" tool. On a run, I was shown the standard permission dialog (Deny / Allow for all scheduled runs / Allow once) and selected "Allow for all scheduled runs."
What Should Happen?
Expected behavior: Future scheduled runs of this task should send the Gmail message without re-prompting, since I explicitly approved it for all scheduled runs.
Actual behavior: The very next scheduled run prompted for the same permission again, as if the "allow for all" choice was never saved.
Error Messages/Logs
Steps to Reproduce
Steps to reproduce:
Create a scheduled task that uses a connector tool requiring approval (in my case, Gmail send_message).
Run it once; when the permission dialog appears, choose "Allow for all scheduled runs."
Let the task fire again on its schedule (or trigger it manually).
Observe that the same permission dialog appears again instead of running silently.
Claude Model
None
Is this a regression?
I don't know
Last Working Version
_No response_
Claude Code Version
2.1.251.
Platform
Anthropic API
Operating System
Windows
Terminal/Shell
Other
Additional Information
Environment: Claude Cowork, scheduled task (cron-based), Gmail connector.
Related reports: This looks like the same class of bug as:
https://github.com/anthropics/claude-code/issues/59302
https://github.com/anthropics/claude-code/issues/32199
https://github.com/anthropics/claude-code/issues/47180
https://github.com/anthropics/claude-code/issues/46205
https://github.com/anthropics/claude-code/issues/33027