Cowork: 'Always Allow' permission does not persist for scheduled tasks - Chrome tools re-prompt every 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?

In Cowork mode, scheduled tasks that use Chrome browser tools are prompted for permission on every single run, despite the user selecting "Always Allow" repeatedly. The permission does not persist across task runs.

Steps to reproduce:

1. Create a scheduled task in Cowork that uses Chrome browser tools (e.g., LinkedIn scraping via navigate, read_page, javascript_tool)
2. When the task runs, it prompts for Chrome browser tool permission
3. Click "Always Allow"
4. Wait for the next scheduled run of the same task
5. The task prompts for Chrome permission again - "Always Allow" was not remembered

I have clicked "Always Allow" hundreds of times across multiple sessions, multiple tasks, over weeks of usage. It never persists.

Compounding issue - sidebar only shows ~5 tasks:
The scheduled task sidebar only displays ~5 concurrent task sessions. When more than 5 tasks run simultaneously (common with staggered morning schedules), permission prompts scroll off-screen and become completely inaccessible. The user cannot scroll to them, click into them, or approve them. These tasks hang indefinitely waiting for permission that can never be granted.

This combination - permissions not persisting + limited sidebar visibility - makes Chrome-dependent scheduled tasks essentially broken for any user with more than 5 scheduled tasks.

Impact: I have 14 scheduled tasks. 5 require Chrome. All 5 Chrome-dependent tasks fail when I am not actively monitoring the sidebar at the exact moment they run. I have had to restructure all 14 task prompts to avoid Chrome where possible and gracefully degrade when Chrome is unavailable, but this is a band-aid for what should be a working "Always Allow" feature.

What Should Happen?

1. Selecting "Always Allow" for Chrome browser tools should persist the permission permanently (or at minimum across all runs of that scheduled task) so scheduled runs execute without manual intervention.

1. The scheduled task sidebar should either be scrollable to access all running tasks, or permission prompts should surface as top-level notifications that don't depend on sidebar visibility.

1. Ideally, scheduled tasks should have a way to pre-authorize tool permissions at creation time so they never need interactive approval during unattended runs.

Error Messages/Logs

No error messages - the task simply hangs waiting for permission approval that never comes (because "Always Allow" didn't persist from the previous run, and the permission prompt scrolled off the visible sidebar).

Steps to Reproduce

1. Open Claude Desktop (Cowork mode) on macOS
2. Create a scheduled task that uses Chrome browser tools (e.g., navigate, read_page, javascript_tool)
3. Let the task run on schedule - it will prompt for Chrome browser tool permission
4. Click "Always Allow" when prompted
5. Wait for the next scheduled run of the same task (or manually trigger it)
6. Observe: the task prompts for Chrome permission again despite "Always Allow" being selected previously
7. Repeat steps 4-6 indefinitely - permission never persists

To observe the sidebar issue:

1. Create 6+ scheduled tasks with overlapping run times
2. When they all run, only ~5 are visible in the sidebar
3. Tasks below the fold that need permission approval are completely inaccessible and hang forever

Environment:

• macOS (MacBook Pro 2021)
• Claude Desktop latest version (Cowork mode)
• Multiple Chrome browser MCP tools affected: navigate, read_page, find, computer, javascript_tool, tabs_context_mcp
• Issue persists across app restarts, new sessions, weeks of usage
• Related: Issue #32188 (session corruption - separate bug, same user)

Claude Model

None

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

Claude Desktop (Cowork mode) - latest version as of Mar 8, 2026

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Workaround applied: All 14 scheduled task prompts have been restructured to either avoid Chrome browser tools entirely (using MCP APIs instead) or gracefully degrade when Chrome permission is unavailable. This is a significant workaround that reduces functionality for tasks that genuinely need Chrome (LinkedIn scraping, Twitter posting, applicant research).

Suggested fix approaches:

1. Make "Always Allow" actually persist permanently per tool category
2. Allow scheduled tasks to pre-authorize tool permissions at creation time
3. Add a global setting: "Allow all scheduled tasks to use Chrome browser tools without prompting"
4. At minimum: make the sidebar scrollable so ALL running tasks are accessible for permission approval

Related issue: #32188 (NDJSON telemetry parsing causing session corruption and destroying all scheduled tasks)