[BUG] Windows 2.1.267: session state becomes inconsistent after auto-compaction (false continuation, missing attachments, stale sessions appear recent)

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?

Preflight Checklist

• [x] I searched existing issues. There are related reports, but I did not find one covering this exact combination on Claude Code 2.1.267.
• [x] This report is about one session-state/history integrity regression with several correlated symptoms.
• [x] Reproduced/observed on Claude Code 2.1.267.

What's Wrong?

On Windows, Claude Code session state/history became unreliable during a long coding session. Three correlated symptoms appeared:

1. An active session was silently auto-compacted and then rewritten as if it were a resumed/continued conversation.

• I started the session normally. I did not run /compact, /resume, or intentionally continue another session.
• About 12 minutes later Claude Code inserted a compaction boundary and a synthetic continuation summary beginning with wording equivalent to:

This session is being continued from a previous conversation that ran out of context.

• The local JSONL proves the compaction was automatic:

Timestamp  : 2026-09-09T21:26:59.023Z
Trigger    : auto
PreTokens  : 1096859
PostTokens : 9229
Version    : 2.1.267

The original user prompt began at 2026-09-09T21:14:55.253Z, so this happened roughly 12 minutes into the same active session.
This wording is misleading because the user did not manually resume/continue anything.
The original attachment/context set stopped being reliably represented after compaction.
The original request included multiple context files attached to the prompt.
After the automatic compaction/continuation boundary, those original attachment chips/files were no longer available in the session UI the way they had been at the start.
The compaction summary references the old context by name, but the actual attached-file state shown by the client no longer matches what was originally supplied.
Other/stale files have also appeared in session surfaces unexpectedly.
Old sessions are suddenly surfacing at the top of Recent/Ungrouped with fresh-looking activity times even though I did not rerun them.
Sessions/prompts that actually ran several days to about a week earlier have appeared at the top of the recent-session feed showing values like 1h or 5h.
I did not rerun those prompts.
Local transcript search still finds their older original content and timestamps.
I have not yet proven whether these fresh timestamps are only session-file/index metadata touches or whether some background path is actually re-opening/reprocessing the sessions, so I am reporting this observation separately from the proven auto-compaction record above.

This makes the sidebar/session UI unsafe to use as evidence of what actually ran or when. I had to recover the authoritative session by searching ~/.claude/projects/**/*.jsonl manually.

### What Should Happen?

- Auto-compaction inside an active session should be clearly labeled as automatic compaction of the current session, not as if the user intentionally resumed another conversation.
- Compaction should preserve/rebind the original attachment/context state, or clearly show which attachments were dropped and why.
- Old sessions should not be moved to the top of Recent/Ungrouped or shown with fresh-looking activity times merely because background metadata/bookkeeping touched a transcript.
- The session picker should distinguish:
- actual user/assistant activity time,
- metadata/index/file modification time,
- compaction time.
- A user should not need to hand-parse .jsonl files to determine which session actually ran and which transcript contains the real implementation result.

### Error Messages/Logs

```shell
There was no explicit error message when the session compacted or when old sessions later appeared recent.

The strongest reproducible evidence is the compact_boundary record in the local JSONL:

trigger: auto
preTokens: 1096859
postTokens: 9229
Claude Code version: 2.1.267

The generated continuation summary was recorded immediately after that boundary as a user-style compact-summary record.

Steps to Reproduce

There was no explicit error message when the session compacted or when old sessions later appeared recent.

The strongest reproducible evidence is the compact_boundary record in the local JSONL:

trigger: auto
preTokens: 1096859
postTokens: 9229
Claude Code version: 2.1.267

The generated continuation summary was recorded immediately after that boundary as a user-style compact-summary record.

Steps to Reproduce / Evidence Collection

The issue is easiest to verify from the local transcript rather than the sidebar:

Run a long, tool-heavy Claude Code session on a large-context model on Windows.
Do not run /compact or /resume.
Let the session continue until Claude Code auto-compacts it.
Inspect the transcript at:
~/.claude/projects/<project>/<session-id>.jsonl
Find type:"system", subtype:"compact_boundary" and inspect compactMetadata.trigger.
In my case it is auto, followed by a synthetic continuation summary that says the conversation is being continued from a previous conversation that ran out of context.
Compare the attachment/context UI before and after the boundary.
Separately, keep several older sessions in history for days, then inspect Recent/Ungrouped. In my case old sessions reappeared at the top with fresh-looking 1h/5h activity despite no intentional rerun.
Compare those sidebar times with the newest real conversational timestamp in each corresponding .jsonl.

PowerShell used to prove the compaction trigger:

$path = "$HOME\.claude\projects\<project>\<session-id>.jsonl"

[System.IO.File]::ReadLines($path) | ForEach-Object {
try { $j = $_ | ConvertFrom-Json -ErrorAction Stop } catch { return }

if ($j.type -eq "system" -and $j.subtype -eq "compact_boundary") {
[pscustomobject]@{
Timestamp = $j.timestamp
Trigger = $j.compactMetadata.trigger
PreTokens = $j.compactMetadata.preTokens
PostTokens = $j.compactMetadata.postTokens
Version = $j.version
}
}
}

Observed output:

Timestamp : 2026-09-09T21:26:59.023Z
Trigger : auto
PreTokens : 1096859
PostTokens : 9229
Version : 2.1.267

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.267

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

Possibly related:

#92434 — auto-compaction/context-window behavior
#92949 — stale context re-injected during auto-compaction
#92209 — Windows local session transcript persistence problems
#90888 — session/chat history missing on Windows
#82914 — pre-compaction history remains on disk but is difficult to access in product UI
Impact

This is high impact for long-running coding/security work because I can no longer trust the client UI to tell me:

which session actually ran,
when it ran,
whether a prompt was rerun,
whether I am looking at the original or compacted context,
or whether the attachment set still corresponds to the original request.

I nearly reran a large implementation prompt because its real result appeared to be missing. The only reason I recovered it was by manually searching the local JSONL transcripts.