[FEATURE] Add a persistent default output folder setting for Cowork sessions

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

Every time a new Cowork session starts, output files are saved to a deeply nested internal path under AppData\Roaming\Claude\local-agent-mode-sessions\...\outputs. Clicking "View in folder" in Windows frequently results in a "Location is not available" error, as the path may have been cleaned up between sessions or is too deeply nested for reliable Explorer access. There is currently no way to configure a persistent default output directory, forcing users to manually connect a folder at the start of every single session.

Proposed Solution

Add a global setting in Claude Desktop (e.g., Settings → Cowork or Settings → Files) that allows users to specify a default output directory (e.g., C:\Users\{username}\Desktop\AI-Workspace). When a new Cowork session starts, this folder should be automatically mounted and used as the output destination without any manual user action.

Alternative Solutions

A per-session prompt that remembers the last-used folder and offers one-click re-connection
A "pin folder" option in the Cowork sidebar that persists across sessions
A CLI flag or config file (claude_desktop_config.json) to set the default path for advanced users

Priority

High - Significant impact on productivity

Feature Category

File operations

Use Case Example

I am building an intelligent "Second Brain" system centered on Claude Cowork and Claude Code. Outputs from various work tools are consolidated into a single knowledge base folder. Obsidian indexes this folder, and Claude Code queries it — forming a persistent, searchable, AI-augmented knowledge graph. For this to work, all Cowork outputs must automatically land in a predictable, user-controlled location. Manual folder connection every session breaks this integration.

Additional Context

OS: Windows
Claude Desktop version: latest (April 2026)
Usage pattern: daily Cowork sessions for hospital marketing research, content creation, and knowledge management
The internal AppData path is not only hard to access but also unreliable — sessions may clean up their output directories, making previously saved files inaccessible
Suggested bonus: optional sub-folder organization by date or session name (e.g., AI-Workspace/2026-04-13_session-name/)
Suggested fallback: if the default folder is unavailable, prompt the user rather than silently saving to AppData