[FEATURE] Session pinning, reordering, and sort-by-last-activity in sidebar

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

The sidebar currently sorts sessions by creation date (newest first). There is no way to pin, reorder, or sort sessions by last activity. For developers actively working across multiple projects, this makes it difficult to keep priority sessions accessible at the top of the sidebar.

For example, I work across 3-4 active projects simultaneously (a geospatial dashboard, a social listening app, a Supabase-to-Convex migration, etc.). Sessions for these projects get buried as I create new sessions for one-off tasks. The only way to surface an active project session is to scroll through the list or use search.

Session naming (#2112) was a great addition, but without the ability to control session order, named sessions still get lost in the chronological list.

Proposed Solution

Three complementary features for session organization:

1. Pin/Star sessions

• Allow users to pin sessions to the top of the sidebar
• Pinned sessions stay at the top regardless of creation date
• A simple star/pin icon toggle on hover would suffice
• Pinned sessions could have their own section above unpinned sessions

2. Sort by last activity

• Add a sort option (alongside the existing Status/Environment filters) to sort by:
• Created (current default)
• Last activity (most recently used session at top)
• Sorting by last activity means simply resuming and working in a session bumps it to the top, which is the natural workflow for active projects

3. Manual drag-to-reorder (nice to have)

• Allow users to manually drag sessions to reorder them
• This gives full control over sidebar priority
• Lower priority than pin and sort-by-activity

Alternative Solutions

Current workarounds that are insufficient:

• Starting fresh sessions with priority names like [1] Project Name — works for visual scanning but clutters the session list and loses context from prior sessions
• Using search — functional but adds friction for frequently accessed sessions
• Archiving old sessions — helps reduce clutter but doesn't solve ordering of active sessions

Priority

Nice to have

Feature Category

UI/UX

Use Case Example

Developer working on 3 active projects:

Current sidebar (sorted by creation date):

Random question I asked today          · 10 min ago
[3] Mobility Dashboard — deck.gl viz   · Feb 5
[2] ScentTrak — Updates                · Tue
[1] GeoAudiences — Phase 5             · Thu
Old session I don't need                · Jan 28
Another old session                     · Jan 27

Desired sidebar (with pinning + sort by last activity):

📌 Pinned
  GeoAudiences — Phase 5               · Thu
  ScentTrak — Updates                   · Tue
  Mobility Dashboard — deck.gl viz      · Feb 5

Recent
  Random question I asked today         · 10 min ago
  Old session I don't need              · Jan 28
  Another old session                   · Jan 27

Related Issues

• #2112 — Session naming (closed/completed) — naming is great but order control is the missing piece
• #21559 — Rename chat sessions (open)
• #18276 — Customizing session/tab names (closed/completed)
• #24801 — Rename sessions in VSCode sidebar (open)

Additional Context

The existing filter dropdown (Status: Active/Archived/All, Environment: Local/Cloud/All) would be a natural place to add a "Sort by" option (Created / Last Activity). Pinning could be a separate UI element (star icon on hover).