[BUG] Cowork scheduled tasks missing from desktop sidebar — only subset rendered; macOS; tasks exist on disk and run correctly

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?

Cowork scheduled tasks are not all appearing in the Claude Desktop sidebar on macOS. Only one of three registered tasks is rendered in the Scheduled section, even though all three exist on disk under ~/Documents/Claude/Scheduled/ and are running on schedule.

When the assistant calls list_scheduled_tasks via the MCP tool layer, all three tasks are returned with enabled: true and correct nextRunAt timestamps. The scheduler backend is functioning. I confirmed end-to-end by manually triggering one task, which executed correctly (it read a Slack channel, matched messages, and sent a DM as designed). The desktop sidebar UI is the only thing broken.

Visible in sidebar:

• lore-monday-gtm-ritual (the oldest task)

Registered and on disk, but NOT visible in sidebar:

• weekly-lore-linkedin-comment-targets
• forward-lore-alerts-signups (created most recently)

This appears related to but distinct from:

• #50928 / #49942: entire Schedule entry missing on Windows (mine is partially visible)
• #48495: sidebar truncating session list (closest match in symptom; mine is the Scheduled subsection)
• #54524 / #55045: routines missing from sidebar (Claude Code routines, not Cowork scheduled tasks)

Filing this as a Cowork-specific report on macOS because existing reports are mostly Windows-focused or about Claude Code routines, and Cowork scheduled tasks are a separate local-only feature (stored under ~/Documents/Claude/Scheduled/, not synced to claude.ai web).

What Should Happen?

All registered scheduled tasks present under ~/Documents/Claude/Scheduled/ should appear in the Claude Desktop sidebar under the Scheduled section, matching what list_scheduled_tasks returns.

Error Messages/Logs

None surfaced in the UI. No visible console errors.

Steps to Reproduce

1. In Cowork mode on macOS, create three scheduled tasks via the assistant (different cron schedules, different prompts).
2. Confirm tasks exist via the assistant calling mcp__scheduled-tasks__list_scheduled_tasks — all three returned with enabled: true.
3. Confirm three folders exist at ~/Documents/Claude/Scheduled/, each containing a SKILL.md.
4. Open the Claude Desktop sidebar and locate the Scheduled section.
5. Expected: all three tasks listed.
6. Actual: only the earliest-created task is listed. The two more recent ones are missing.
7. Quit Claude with Cmd+Q (full quit, not window close) and reopen. No change.
8. The hidden tasks still run on schedule (verified by manually triggering one — it produced the expected output end-to-end).

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

1.8089.1

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

• Tasks fire correctly on schedule despite the UI rendering bug. The backend scheduler reads from ~/Documents/Claude/Scheduled/ directly, independent of the sidebar.
• Cmd+Q and reopen does not refresh the sidebar.
• All three task folders are present and readable on disk.
• The visible task is lore-monday-gtm-ritual, created earliest. The two hidden tasks (weekly-lore-linkedin-comment-targets, forward-lore-alerts-signups) were created more recently. The pattern suggests a possible cap or ordering bug — the sidebar may be rendering only the first N entries or only entries below some staleness threshold.
• The tasks are local-only (not cloud-synced), so this cannot be reproduced by inspecting account state on the server. The desktop app must be inspected against the local ~/Documents/Claude/Scheduled/ directory on the reporter's machine.
• A useful diagnostic would be to dump whatever query the sidebar runs against the local scheduled-tasks store and compare to the output of list_scheduled_tasks.

Related issues: #50928, #49942, #54524, #55045, #48121, #48495, #29022, #35131