session group

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Title: Session grouping regression — groups no longer follow working directory, and new sessions land in "Ungrouped"

Summary

Session grouping in the Claude Code app changed and is now much harder to use than before. Previously sessions were grouped sensibly (matching their working directory); now grouping is disconnected from the working directory and requires constant manual cleanup.

Two distinct problems:

Groups no longer match the working directory. Sessions that have a working directory still show up as "Ungrouped." A large number of my existing sessions are now Ungrouped even though every one of them has a valid working directory. It looks like grouping is now a separate manual concept instead of being derived from the working directory the way it used to be.
New sessions don't inherit the active group. When I select/activate a group and then start a new session, the new session does not get placed in that active group — it drops into "Ungrouped." So for every new session I have to right-click it and manually "Move to group." This is repetitive friction that wasn't there before.
Expected behavior (how it worked before)

Sessions are grouped by their working directory automatically, OR
At minimum, a new session created while a group is active should be placed into that active group — not into Ungrouped.
Actual behavior

Existing sessions with a valid working directory appear as Ungrouped.
New sessions created inside an active group go to Ungrouped and must be manually moved each time.
Steps to reproduce (problem #2)

Select/activate an existing group.
Create a new session.
Observe: the new session appears under "Ungrouped" instead of inside the active group.
Must right-click the session → Move to group, every time.
Impact

This used to be a smooth, automatic experience. Now it requires manual grouping for every new session and a one-time manual re-grouping of many existing sessions. Please either restore automatic grouping by working directory, or make new sessions inherit the currently active group.

Environment

OS: Windows 11 Pro (10.0.26200)
Claude Code app (desktop)

What Should Happen?

Session grouping should keep sessions organized automatically and require no manual cleanup:

Sessions should group by their working directory automatically. Every session that has a working directory should appear under the group for that directory — not in "Ungrouped." This is how it worked before, and it kept the sidebar organized without any manual effort.
A new session created while a group is active should be placed in that active group. When I have a group selected and start a new session, that session should land inside the active group automatically. I should not have to right-click → "Move to group" after creating each session.
Existing group assignments should be preserved. Sessions that already have a working directory (or were grouped) should stay grouped across app restarts and preference changes — they should not silently fall back to "Ungrouped."
In short: grouping should be automatic and persistent (by working directory, and/or by inheriting the active group), so the session list stays organized the way it used to — without manual re-grouping for every new session.

Error Messages/Logs

Steps to Reproduce

Problem 1 — existing sessions show as Ungrouped despite having a working directory:

Open the Claude Code app and look at the session list/sidebar.
Observe sessions that each have a valid working directory.
Notice many of them appear under "Ungrouped" rather than grouped by their working directory (this used to happen automatically).
Problem 2 — new sessions don't inherit the active group:

Select/activate an existing group in the sidebar.
While that group is active, create a new session.
Observe: the new session appears under "Ungrouped" instead of inside the active group.
To fix it, right-click the session → "Move to group" → select the group.
Repeat the manual move for every new session created.
Expected: New sessions created while a group is active should land in that active group (and/or sessions should auto-group by their working directory as before).

Actual: New sessions always land in "Ungrouped" and must be manually moved each time; existing sessions with a working directory also show as Ungrouped.

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Version 1.13576.0 (1290fc)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

_No response_