[FEATURE] Desktop app: cache and show last 3-4 working directories in the new-session folder picker

Preflight Checklist

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

Problem Statement

I regularly work across multiple projects and switch between a handful of working directories throughout the day. In the Claude Code desktop app, starting a new session means opening the folder picker and navigating to the project each time.

The picker's behavior is also inconsistent: sometimes it shows the couple of directories I use most often, and other times it only shows the single last-used directory. There's no reliable, quick way to jump between my frequent projects.

Proposed Solution

Cache the last 3–4 working directories and consistently display them in the new-session folder picker, so I can select a recent project in one click instead of navigating the filesystem. The displayed list should remain stable across app restarts.

Nice-to-haves:

• A setting to control how many recent directories are remembered (e.g. recentDirectoriesCount).
• Ability to "pin" / favorite directories so they always appear.

Alternative Solutions

• Launching the CLI from the target folder, or keeping per-project desktop shortcuts, to avoid the picker entirely.
• Using /add-dir <path> mid-session — works, but it isn't persisted across sessions and doesn't help the new-session flow.

Priority

High - Significant impact on productivity

Feature Category

Other (Desktop app — new-session folder picker / working-directory selection)

Use Case Example

1. I have three repos I bounce between during the day.
2. I open the desktop app and click "+ New session".
3. Today I have to browse the filesystem to the right repo, and the picker only reliably remembers the last one.
4. With this feature, the picker would show my last 3–4 working directories and I'd select the one I want in a single click.

Additional Context

• Platform: Windows 11, Claude Code desktop app.
• The inconsistent display (sometimes multiple recent dirs, sometimes only the last one) may itself be a bug worth investigating alongside this request.
• Related existing issues, included for triage (each is distinct from this request):
• #62843 — project switcher / change working directory within an active session (this request targets the new-session picker instead)
• #54911 — Desktop Recents to enumerate ~/.claude/projects/ directly
• #59282 — Desktop "Recent" sort uses stale timestamps
• #56067 — group recent sessions in sidebar by project / working directory