[FEATURE] Cowork Scheduled Tasks: Allow selecting multiple folders per task

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

When configuring a scheduled task in Cowork, the folder picker only allows selecting a single folder. Clicking a new folder deselects the previous one — there is no multi-select capability. This is limiting for workflows that naturally span multiple project directories.

Proposed Solution

The folder picker in scheduled task configuration should support selecting multiple folders, all of which are mounted and accessible during the task run — consistent with how userSelectedFolders works in regular Cowork sessions.

Alternative Solutions

Currently the only workaround is to point the task at a common parent folder, which is not always possible when folders are in unrelated paths or belong to separate repositories. Restructuring existing folder hierarchies just to accommodate the tool is counterproductive.

Priority

High - Significant impact on productivity

Feature Category

Other

Use Case Example

For example, a daily support task may need access to both a main working folder and a separate project folder like user manual that has own git repository. Currently the only workarounds are to point the task at a common parent folder (not always possible if folders are in unrelated paths)

Additional Context

Current Behavior

Only one folder can be selected per scheduled task. Selecting a second folder deselects the first.

Possible related Issues

• #52956 — present_files regression rejecting non-primary userSelectedFolders mounts (related multi-folder limitation in Cowork sessions)
• #38309 — Multi-folder workspace support request for Claude Code sessions

Environment

• Claude Desktop (macOS) - Claude 1.13576.0 (1290fc) 2026-06-16T05:46:10.000Z
• Cowork scheduled tasks