[BUG] BHR Monday Report Update — Weekly Automation

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?

/schedule fails repeatedly with "We're having trouble connecting with your remote claude.ai account to set up a scheduled task." Logs show [CoworkScheduledTasksApi] getAllScheduledTasks: Scheduled tasks not initialized warnings. Persists across app restart and after running /setup-cowork in the Cowork window. Other Cowork features work; only the scheduled-tasks subsystem appears uninitialized.

What Should Happen?

Running /schedule with a valid recurring or one-time schedule request should create a scheduled task on the user's claude.ai account and confirm success in the chat. The Cowork scheduled-tasks subsystem should initialize automatically on app launch (or on first /schedule invocation) so that subsequent calls succeed without manual setup.

Error Messages/Logs

We're having trouble connecting with your remote claude.ai account to set up a scheduled task. Please try /schedule again in a few minutes.


From `~/Library/Logs/Claude/main.log`:


2026-05-19 15:12:27 [warn] [CoworkScheduledTasksApi] getAllScheduledTasks: Scheduled tasks not initialized
2026-05-19 15:12:27 [warn] [CoworkScheduledTasksApi] getAllScheduledTasks: Scheduled tasks not initialized
2026-05-19 15:12:27 [warn] [CoworkScheduledTasksApi] getAllScheduledTasks: Scheduled tasks not initialized
2026-05-19 15:12:27 [warn] [CoworkScheduledTasksApi] getAllScheduledTasks: Scheduled tasks not initialized



2026-05-12 08:46:51 [info] [elicitation] skill not found: skill=setup-cowork via=UserPromptSubmit
2026-05-19 15:27:23 [info] [elicitation] skill not found: skill=setup-cowork via=PreToolUse


Related transport-layer errors on other Cowork-backed endpoints:


2026-05-10 04:44:53 [warn] [PluginsFetcher] fetchAccountScopedRemotePlugins: listAccountMarketplaces failed, returning []: Error: [remoteMarketplaceClient] transport error: This operation was aborted
2026-05-19 05:41:40 [warn] [remoteManagedSettings] fetch failed: DOMException [AbortError]: This operation was aborted

Steps to Reproduce

1. Open Claude Code on macOS (claude.ai desktop app).
2. In any session, type /schedule followed by a valid recurring schedule request — for example: /schedule a recurring task every Monday at 9am Pacific to Slack-DM me reminding me to run "my BHR Monday update".
3. Submit the command.
4. Observed: error returned in chat: We're having trouble connecting with your remote claude.ai account to set up a scheduled task. Please try /schedule again in a few minutes.
5. Retry /schedule with the same prompt — same error.
6. Quit Claude (Cmd+Q), relaunch the app, retry /schedule — same error.
7. Open the main Cowork window (separate from Claude Code) and run /setup-cowork; complete the wizard.
8. Return to Claude Code, retry /schedule — same error.
9. Confirm ~/Library/Logs/Claude/main.log contains repeated [CoworkScheduledTasksApi] getAllScheduledTasks: Scheduled tasks not initialized warnings and [elicitation] skill not found: skill=setup-cowork entries.

Environment:

• macOS (Apple Silicon — m3mb-arooney)
• Claude.ai desktop app with Claude Code
• claude.ai account active and logged in (per ~/Library/Logs/Claude/main.log: claude.ai account active and logged in on 2026-05-14)
• coworkScheduledTasksEnabled: true and ccdScheduledTasksEnabled: true in ~/Library/Application Support/Claude/claude_desktop_config.json

Workarounds attempted (all unsuccessful):

• App restart
• Running /setup-cowork in the Cowork window
• Direct call to local mcp__scheduled-tasks__create_scheduled_task MCP tool — returns This tool requires user interaction and is unavailable in unsupervised mode

Note: Other Cowork-backed features (plugin fetcher, Slack slack_schedule_message, BambooHR MCP, web search) are working in the same session — the failure appears isolated to the scheduled-tasks subsystem.

Claude Model

Opus

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

N/A — Claude Code runs inside the Claude desktop app (v1.7196.3) on macOS; no standalone CLI is installed. Internal Claude Code build per logs: 1.1062.0

Platform

Other

Operating System

macOS

Terminal/Shell

Other

Additional Information

Platform: Claude Code (running inside Claude desktop app v1.7196.3 on macOS 15.7.4 / Apple Silicon)

Terminal/Shell: N/A — Claude Code runs inside the Claude desktop app, not a standalone terminal. Underlying shell is /bin/zsh if relevant for Bash tool calls.