[BUG] claude desktop-code lost after restart previous chats, cowork dont work

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?

To: support@anthropic.com
Subject: Re: Ticket #215473399132693 - Day 3 update: Cowork stuck, conversations still lost, no human response

Hello,

This is my fourth follow-up on ticket #215473399132693. I have still NOT received a single human response -- only automated/AI replies for 3 days.

USER JOURNEY (context for understanding the setup):
----------------------------------------------------

1. Created claude.ai account, started using Claude chat in browser
2. Upgraded to Claude Pro (paying customer)
3. Installed Claude Desktop App (CDT) on macOS under user "heikki"
4. Started using Claude Code; CLI was installed alongside CDT
5. For security reasons, created a dedicated macOS user "claude"
6. Moved CDT to run exclusively under macOS user "claude"
7. Used CDT to migrate old Claude sessions and logs from user/heikki to user/claude
8. At some point discovered that some sessions had gone missing
9. Used CDT to investigate the problem and reported to support@anthropic.com
10. Discovered pattern: new chats are visible as long as CDT is not restarted. After restart, only the same old sessions remain visible -- new ones disappear
11. March 10: CDT code and cowork sessions would not start at all
12. March 11: CDT Cowork feature completely non-functional (stuck on "Starting...")

ISSUE TIMELINE:

• March 9: 54+ conversations lost after app update. New conversations also disappearing mid-session (sessions hang, then vanish from sidebar).
• March 10: Cannot start ANY new conversations in DTA. App accepts input but does not respond. Code and Cowork sessions fail to start.
• March 11 (today): Performed full Mac restart + CDT restart. Conversations partially restored (can see some in sidebar). However, Cowork feature is stuck on "Starting Claude's workspace..." and will not proceed.

KEY FINDING -- SESSION PERSISTENCE BUG:
----------------------------------------
New conversations created in CDT are visible ONLY until CDT is restarted. After restart, they disappear and only previously existing sessions remain. This suggests sessions are held in memory/local state but not properly synced or persisted to the server.

TODAY'S DIAGNOSTICS (March 11):
-------------------------------
After restart, I investigated the Cowork issue via terminal (Claude Code CLI, running under same user):

1. CDT process is running (PID confirmed)
2. Claude Code CLI process is running inside CDT
3. Virtualization VM process IS running (com.apple.Virtualization.VirtualMachine, using 1.5GB RAM)
4. claude-code-vm files exist: version 2.1.72, .verified flag present
5. Config shows: coworkNetworkMode: "gvisor", coworkScheduledTasksEnabled: true
6. Cowork UI remains stuck on "Starting Claude's workspace..." despite VM being active

This means the VM starts successfully but CDT's UI cannot connect to it or does not detect it as ready.

Attempted fixes today:

• killall "Claude" + restart CDT -- no change
• Full Mac restart -- conversations partially came back, but Cowork still stuck
• Switching tabs (Chat <-> Cowork) -- no change

FULL ISSUE SUMMARY:
-------------------

1. 54+ conversations lost (March 9) -- server-side data loss, UUIDs available from local storage analysis (provided in original ticket)
2. Session persistence bug -- new chats vanish on CDT restart, not synced to server
3. New conversations disappearing mid-session (March 9) -- sessions hang then vanish
4. Cannot start new conversations (March 10) -- app accepts input, no response
5. Cowork stuck on "Starting..." (March 11) -- VM runs but UI cannot connect
6. NO human support response in 3 days

WHAT I NEED:
------------

1. A HUMAN response -- automated replies cannot resolve these issues
2. Engineering investigation into:

a. Server-side conversation restoration (54 UUIDs provided previously)
b. Session persistence bug: why new conversations are lost on CDT restart
c. Why Cowork VM starts but UI stays on "Starting..." (possible IPC/socket issue between CDT and VM)
d. Why sessions were hanging and disappearing (March 9-10)

1. Status update on the investigation
2. Expected timeline for resolution

SYSTEM INFO:
------------
Account: Claude Pro
Platform: macOS (Darwin 25.3.0)
App version: Claude Desktop 1.1.5749
Claude Code VM: 2.1.72 (verified)
Cowork network mode: gvisor
Setup: CDT runs under dedicated macOS user "claude" (not default user)
Original ticket: #215473399132693

I am a paying Pro customer and have been unable to fully use the service for 3 consecutive days. This is unacceptable without any human acknowledgment.

Thank you,
Heikki

What Should Happen?

claude desctop should work

Error Messages/Logs

To: support@anthropic.com
Subject: Re: Ticket #215473399132693 - Day 3 update: Cowork stuck, conversations still lost, no human response

Hello,

This is my fourth follow-up on ticket #215473399132693. I have still NOT received a single human response -- only automated/AI replies for 3 days.

USER JOURNEY (context for understanding the setup):
----------------------------------------------------
1. Created claude.ai account, started using Claude chat in browser
2. Upgraded to Claude Pro (paying customer)
3. Installed Claude Desktop App (CDT) on macOS under user "heikki"
4. Started using Claude Code; CLI was installed alongside CDT
5. For security reasons, created a dedicated macOS user "claude"
6. Moved CDT to run exclusively under macOS user "claude"
7. Used CDT to migrate old Claude sessions and logs from user/heikki to user/claude
8. At some point discovered that some sessions had gone missing
9. Used CDT to investigate the problem and reported to support@anthropic.com
10. Discovered pattern: new chats are visible as long as CDT is not restarted. After restart, only the same old sessions remain visible -- new ones disappear
11. March 10: CDT code and cowork sessions would not start at all
12. March 11: CDT Cowork feature completely non-functional (stuck on "Starting...")

ISSUE TIMELINE:
- March 9: 54+ conversations lost after app update. New conversations also disappearing mid-session (sessions hang, then vanish from sidebar).
- March 10: Cannot start ANY new conversations in DTA. App accepts input but does not respond. Code and Cowork sessions fail to start.
- March 11 (today): Performed full Mac restart + CDT restart. Conversations partially restored (can see some in sidebar). However, Cowork feature is stuck on "Starting Claude's workspace..." and will not proceed.

KEY FINDING -- SESSION PERSISTENCE BUG:
----------------------------------------
New conversations created in CDT are visible ONLY until CDT is restarted. After restart, they disappear and only previously existing sessions remain. This suggests sessions are held in memory/local state but not properly synced or persisted to the server.

TODAY'S DIAGNOSTICS (March 11):
-------------------------------
After restart, I investigated the Cowork issue via terminal (Claude Code CLI, running under same user):

1. CDT process is running (PID confirmed)
2. Claude Code CLI process is running inside CDT
3. Virtualization VM process IS running (com.apple.Virtualization.VirtualMachine, using 1.5GB RAM)
4. claude-code-vm files exist: version 2.1.72, .verified flag present
5. Config shows: coworkNetworkMode: "gvisor", coworkScheduledTasksEnabled: true
6. Cowork UI remains stuck on "Starting Claude's workspace..." despite VM being active

This means the VM starts successfully but CDT's UI cannot connect to it or does not detect it as ready.

Attempted fixes today:
- killall "Claude" + restart CDT -- no change
- Full Mac restart -- conversations partially came back, but Cowork still stuck
- Switching tabs (Chat <-> Cowork) -- no change

FULL ISSUE SUMMARY:
-------------------
1. 54+ conversations lost (March 9) -- server-side data loss, UUIDs available from local storage analysis (provided in original ticket)
2. Session persistence bug -- new chats vanish on CDT restart, not synced to server
3. New conversations disappearing mid-session (March 9) -- sessions hang then vanish
4. Cannot start new conversations (March 10) -- app accepts input, no response
5. Cowork stuck on "Starting..." (March 11) -- VM runs but UI cannot connect
6. NO human support response in 3 days

WHAT I NEED:
------------
1. A HUMAN response -- automated replies cannot resolve these issues
2. Engineering investigation into:
   a. Server-side conversation restoration (54 UUIDs provided previously)
   b. Session persistence bug: why new conversations are lost on CDT restart
   c. Why Cowork VM starts but UI stays on "Starting..." (possible IPC/socket issue between CDT and VM)
   d. Why sessions were hanging and disappearing (March 9-10)
3. Status update on the investigation
4. Expected timeline for resolution

SYSTEM INFO:
------------
Account: Claude Pro
Platform: macOS (Darwin 25.3.0)
App version: Claude Desktop 1.1.5749
Claude Code VM: 2.1.72 (verified)
Cowork network mode: gvisor
Setup: CDT runs under dedicated macOS user "claude" (not default user)
Original ticket: #215473399132693

I am a paying Pro customer and have been unable to fully use the service for 3 consecutive days. This is unacceptable without any human acknowledgment.

Thank you,
Heikki

Steps to Reproduce

i'm not a coder

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

1.1.6041

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

USER JOURNEY (context for understanding the setup):
----------------------------------------------------

1. Created claude.ai account, started using Claude chat in browser
2. Upgraded to Claude Pro (paying customer)
3. Installed Claude Desktop App (CDT) on macOS under user "heikki"
4. Started using Claude Code; CLI was installed alongside CDT
5. For security reasons, created a dedicated macOS user "claude"
6. Moved CDT to run exclusively under macOS user "claude"
7. Used CDT to migrate old Claude sessions and logs from user/heikki to user/claude
8. At some point discovered that some sessions had gone missing
9. Used CDT to investigate the problem and reported to support@anthropic.com
10. Discovered pattern: new chats are visible as long as CDT is not restarted. After restart, only the same old sessions remain visible -- new ones disappear
11. March 10: CDT code and cowork sessions would not start at all
12. March 11: CDT Cowork feature completely non-functional (stuck on "Starting...")