[FEATURE] Pinned chats: sort order inconsistent between mobile (recency) and desktop (stale manual order) — add sort modes and a reset

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

Pinned chat ordering is inconsistent across surfaces, and there is no way to reset it.

Mobile app: pinned chats always sort by recency (last activity). This is great — active work floats to the top, so I can glance at the top of my pins to see which sessions are done or ready for review.

Desktop app: once you have ever manually dragged a pin, the app persists an explicit manual order (a local pinnedOrder — see #50391, where logout wipes it). From then on:

• The manual order is frozen at whatever it was when you last dragged, even if that was months ago
• Newly pinned chats get inserted into that stale manual list at an unpredictable position (they appear "in the middle") rather than sorted or consistently placed
• There is no UI to switch back to recency sorting, and no way to clear the manual order short of unpinning everything and re-pinning

New Home tab: as of the July 2026 launch that brings Chat and Cowork together in a Home tab on desktop, this behavior persists for both Chat pins and Cowork pins.

The net effect is that the same pinned list is self-organizing on mobile and a stale, unpredictable mess on desktop.

Proposed Solution

Any or all of:

1. Sort mode for pinned chats — Recency (default) / Manual. Recency matches current mobile behavior; Manual preserves drag-to-reorder for those who want it.
2. "Reset to recency" affordance — a way to clear the persisted manual order without unpinning everything.
3. Predictable insertion in manual mode — new pins go to the top (or bottom) of the pinned section, never the middle.
4. Cross-surface consistency — pin order semantics (or at least the sort mode) should be consistent between mobile and desktop, ideally synced like pin membership is.

Alternative Solutions

Current workaround is to unpin every chat and re-pin — which loses the order entirely and still doesn't restore recency sorting on desktop.

Priority

Medium - Would be very helpful

Feature Category

UI/UX

Related Issues

• #50391 — desktop pinnedOrder stored in localStorage, wiped on logout (confirms the manual-order persistence mechanism)
• #66196 — sidebar project/group sort order (closed)
• #25974 — session pinning/reordering/sort-by-last-activity in Code sidebar (closed as duplicate)

Additional Context

Observed on the Claude desktop app on macOS (Chat + Cowork pins, including the new Home tab) vs the iOS mobile app. Filed from Cowork.