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[BUG] iMessage MCP extension enabled in Cowork settings but never appears in session tools #40703

Description

@zenathar

Description

The iMessage MCP extension is toggled on in Cowork settings UI (with all 4 tools listed: Search Contacts, Read iMessages, Get Unread iMessages, Send iMessage), but none of these tools are ever exposed to the Cowork session. The extension simply does not appear in the deferred tools list.

This is different from #32999 / #21737 (where the tool appeared but failed with an FDA error). Here the tool never loads at all — it is completely absent from the session.

Steps to reproduce

  1. Open Claude Desktop (latest version, March 2026)
  2. Go to Settings → enable iMessage extension (all 4 tools enabled)
  3. Start a new Cowork session
  4. Ask Claude to list available MCP tools or search for iMessage tools
  5. Expected: iMessage tools appear in the deferred tools list
  6. Actual: No iMessage tools found. ToolSearch for "imessage", "sms", "send message", "apple message contact" etc. all return empty results

Environment

What works

All other MCP extensions connect fine in the same Cowork session:

  • Gmail, Slack, Google Calendar, ClickUp, Chrome, Computer Use, PagerDuty, Make.com, AWS — all present and functional

Only iMessage fails to connect silently.

What I have tried

Possibly related issues

Expected behavior

iMessage MCP tools should appear in the Cowork session deferred tools list when the extension is enabled in settings, just like Gmail, Slack, and other extensions do.

Additional context

There is no error banner or message in the Cowork UI indicating that the iMessage extension failed to connect — it fails completely silently. Other MCP connection failures (e.g. Chrome, mcp-registry) at least show a banner. The silent failure makes debugging very difficult for users.

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