[BUG] Windows desktop: claude.ai OAuth connectors show "Connected" but load zero tools into cloud/Cowork sessions after this week's update

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?

Summary

After the desktop app update this week, all claude.ai OAuth connectors
(Gmail, Google Drive, Google Calendar, HubSpot, etc.) show as "Connected"
in the UI but expose zero tools to cloud-based / Cowork chat sessions.
The connectors authenticate fine and appear toggled on, but their tools are
never provisioned into the session — the model reports enabledInChat: false
for every connector and finds no connector tools available.

Environment

• OS: Windows 11
• Claude Desktop version: 1.19367.0
• Broke after: the July 7, 2026 update that rolled out Cowork cloud/remote

sessions to desktop

• Plan: Max

What works vs. what doesn't

• ✅ Native runtime tools (web search, web fetch, file read/write, bash) — work
• ✅ Local device-bridge tools (browser control, local machine access) — work
• ❌ claude.ai OAuth connectors (Gmail, Drive, Calendar, HubSpot, all of them)

— show "Connected" but load no tools into the session

This split isolates the failure to the connector-provisioning path for
cloud sessions specifically — not auth (connectors sign in fine), not the
network (native web tools work), not the desktop bridge (local tools work).

Reproduces across

• Multiple fresh chats
• Multiple computers (same account)
• Disconnect/reconnect of the connector
• Reducing to a single enabled connector at session start

Expected

Enabled connectors' tools are available in cloud/Cowork sessions.

Actual

Connectors report enabledInChat: false and load zero tools; only native
runtime tools and local device-bridge tools are available.

What Should Happen?

When a claude.ai connector is enabled and shows "Connected," its tools
should be available to Claude in cloud/Cowork sessions the same way they
are in a regular browser chat at claude.ai. Enabling Gmail (or any
connector) and starting a cloud session should give Claude that connector's
tools — so a request like "search my Gmail" actually works. The connector's
tools should be provisioned into the session at startup, and the session
should report the connector as enabled/active, not enabledInChat: false
with zero tools loaded.

Error Messages/Logs

Steps to Reproduce

1. Enable one or more claude.ai connectors (e.g. Gmail); confirm they show

"Connected" and toggled on in the chat's Connectors menu.

1. Start a new cloud-based / Cowork chat in the desktop app.
2. Ask Claude to use the connector (e.g. "search my Gmail").
3. Claude has no connector tools available.

Claude Model

Not sure / Multiple models

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

1.19367.0

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

Regular browser chat at claude.ai is unaffected — only cloud/Cowork desktop
sessions fail. Started after the desktop app update this week.