Preflight Checklist

• I have searched existing issues and this hasn't been reported yet
• This is a single bug report (please file separate reports for different bugs)
• I am using the latest version of Claude Code

What's Wrong?

Bug Description

MCP connectors (Datadog, Atlassian/Jira) are not available to scheduled tasks when they fire automatically. The agent cannot see or call any MCP tools — they do not appear in the session's tool set. However, sending any user message into the same session immediately makes the connectors available and functional.

This is not a configuration issue. The connectors are properly connected and work perfectly in interactive chat. The problem is that scheduled task sessions do not initialize MCP connectors until a human interaction triggers the session.

Environment Info

• Platform: Web (claude.ai)
• Product: Claude in Chrome — scheduled tasks
• Connectors affected: Datadog (search_datadog_monitors, analyze_datadog_logs, etc.), Atlassian/Jira (getJiraIssue, searchJiraIssuesUsingJql, createJiraIssue, etc.)
• Connectors confirmed working: Yes, both work immediately after any user message in the same session

Key Observation

This is not a timing issue. Retries with delays don't help. The connectors are genuinely not wired into the session context until a user message arrives. The scheduled task runs in a context where MCP connector initialization simply doesn't happen.

Related Issues

• [BUG] Cowork /schedule skill fails — create_scheduled_task tool not injected into session context (Windows) #29022 — create_scheduled_task tool not injected into Cowork session context
• [BUG] Cowork mode: MCP connectors (Asana, Google Calendar) return 403 errors despite working in Claude Chat #18194 — Cowork mode MCP connectors return 403 despite working in Claude Chat
• [BUG] Cowork MCP connectors lose auth after context compaction — not just server restarts" #34832 — MCP connectors lose auth after context compaction in Cowork
• [BUG] MCP tool not available to model despite successful registration #27159 — MCP tools not available to model despite successful registration

What Should Happen?

Scheduled tasks should have access to the same MCP connectors that are available in interactive chat sessions. The connectors should initialize when the scheduled task session starts, not when a human interacts with it.

Error Messages/Logs

Scheduled tasks fire with no MCP connectors available. All MCP tool calls fail. Sending any user message immediately initializes the connectors and everything works.

Steps to Reproduce

1. Connect Datadog and Atlassian MCP connectors at claude.ai/settings/connectors
2. Verify both work in a normal interactive chat (e.g., "search Jira for PVZAZ-1444" → works)
3. Create a scheduled task that calls MCP tools as its first action (e.g., search_datadog_monitors and getJiraIssue)
4. Let the scheduled task fire on its cron schedule
5. Observe: The agent reports MCP tools are not available / not in the session
6. Send any message into the session (e.g., "use jira to retrieve a single task")
7. Observe: The exact same MCP tools now work immediately

What I've Tried (prompt engineering — none of these work)

Attempt 1: Explicit tool instructions

Added "You already have Datadog and Jira MCP connectors" with tool prefixes — agent still introspected its tool list, found nothing, and bailed.

Attempt 2: "Never inspect tools, just call them"

Added aggressive instructions: never call search_mcp_registry, never claim tools are missing, never suggest reconnecting, just call the tools directly. Agent still could not see or invoke any MCP tools after 5 retry attempts with 20-second delays.

Attempt 3: Retry with backoff

Added warm-up probes (search_datadog_monitors + getJiraIssue) with 5 retries, 20-second delays. All 5 attempts failed. Then a single user message made everything work instantly.

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

No response

Claude Code Version

2.1.78

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Other

Additional Information

This is all in the Claude MacOS app (Claude 1.1.7053 (cc1949) 2026-03-16T22:55:50.000Z)