[FEATURE] Group sessions by project folder and show explicit date/time

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 session sidebar in the Code tab of Claude Desktop has two usability issues that become significant when working on multiple unrelated projects in parallel:

1) No grouping of sessions by project

All sessions are shown in a single flat list, regardless of which project folder they belong to. When working on three or four unrelated codebases at once, sessions from different projects are interleaved with no visual separation, making the list hard to scan and navigate.

The existing filter only supports status (Active / Archived) and environment (Local / Cloud) — there is no way to filter or group by project folder.

2) Only relative timestamps, no actual date/time

Each session row shows only relative timestamps like "2h ago" or "yesterday". When trying to find a session from a week or two back, this is not enough — the user has to click into individual sessions to figure out when they actually happened. The same applies to the Chat tab history.

These two issues compound: a long flat list without dates makes it hard to locate a specific past session, especially across multiple projects.

Proposed Solution

Two related improvements to the session sidebar and the chat view (applicable to both the Code tab and Chat tab where relevant):

1) Grouping and filtering by project

• Automatic grouping of sessions by project folder, with collapsible groups (similar to how IDEs group files by workspace).
• Optional custom grouping: user-defined categories or tags, so sessions can be grouped by client, feature area, status, or any other dimension that fits the user's workflow — not only by folder.
• A toggle or filter to show only sessions from the current project.

2) Explicit date and time on each session row (sidebar)

• Show absolute date and time directly in the sidebar row, alongside or instead of relative timestamps.
• Ideally show both creation time and last-activity time, e.g. "Started: 2026-04-28 09:14 · Last active: 2026-05-02 16:30".
• Apply the same to the Chat tab history list.

3) Date and time on each individual message inside the chat

• Show an explicit timestamp on every message in the conversation — both user messages and Claude's responses.
• The timestamp can appear directly above or below each message bubble.
• This makes it easy to see when a particular exchange happened, which is useful when reviewing long sessions, returning to a session after several days, or correlating decisions with other events (commits, tickets, meetings).
• Could be shown by default, or made toggleable in settings for users who prefer a cleaner view.

All three changes are scoped to UI/UX improvements and would significantly improve usability for anyone juggling multiple parallel projects or returning to long-running sessions, without requiring any backend or storage changes.

Alternative Solutions

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Priority

Medium - Would be very helpful

Feature Category

CLI commands and flags

Use Case Example

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Additional Context

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