[BUG] Cowork does not load ~/.claude/CLAUDE.md at session start

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?

When starting a Cowork session in the Claude desktop app, ~/.claude/CLAUDE.md (user-scoped instructions) is not loaded into context. Claude has no awareness of the file's contents until the user manually pastes them into the chat.

What Should Happen?

Contents of ~/.claude/CLAUDE.md should be loaded into context at the start of every session, consistent with documented Claude Code behavior. The docs state this file applies to "all projects" and is loaded at "every session".

Error Messages/Logs

Steps to Reproduce

1. Create ~/.claude/CLAUDE.md with any standing instructions (e.g. "Always ask for confirmation before write operations")
2. Start a new Cowork session in the Claude desktop app
3. Ask Claude if it has any standing instructions, or attempt an action that should be blocked by the instructions
4. Observe that Claude has no awareness of the file

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Unknown (Cowork — no CLI version available)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This appears to be part of a broader pattern of Cowork not fully honoring the ~/.claude/ directory. See also: #50669 (Cowork only loads 3/27 personal skills from ~/.claude/skills/).

For users relying on CLAUDE.md for safety-critical instructions (e.g. requiring explicit consent before write operations to connected MCP tools), this is a meaningful gap — the guardrails simply aren't in place until the user manually pastes them in.

Platform: macOS, Claude desktop app (Cowork mode)