[BUG] /desktop handoff passes me over but sends me down fruitless re-auth loop

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?

on claude code, /desktop sends my session over to the desktop app, but the desktop app immediately decides I need to re-authenticate (on a newly-authenticated session). A comically unfortunate series of authentication bugs cascades from that. I'm unsure if I should report on a missing SSO login on this report or another.

• No bug report looks like this one, but there might be lingo-barriers here.

What Should Happen?

I would expect the claude code CLI session to activate the Desktop App as it does, and then I carry on.

Error Messages/Logs

On the desktop app:
"Sign in again to continue
For security, Claude Code needs a recent sign-in."

At "Continue with google" (no mention of SSO, still in App)
"Your organization requires SSO authentication"
(no ability to login from here, no mention of SSO:
<img width="464" height="458" alt="Image" src="https://github.com/user-attachments/assets/0346353b-b8ff-4d9c-913a-be065ec2604a" />

Steps to Reproduce

1. recent login at claude.com
2. desktop app recently opened, says "What up next, <your name>" -- suggesting it's authenticated
3. use "claude" at CLI, get frustrated at cut-n-paste not working, choose to send to /desktop
4. type /desktop
5. notice the desktop app brings to front
6. notice the desktop app now says "Claude Code needs a recent sign-in"

<img width="548" height="223" alt="Image" src="https://github.com/user-attachments/assets/ca1b3314-a12c-44f2-87ed-b92b157bc6ee" />

1. you're optimistic: you click the "Sign in again"
2. the desktop app changes to a generic logged-out screen

<img width="735" height="695" alt="Image" src="https://github.com/user-attachments/assets/49a85d4e-fda4-453b-b198-620ad37134a0" />

1. click "Get started" there

Desktop app goes to a signin form without any mention of SSO

<img width="507" height="394" alt="Image" src="https://github.com/user-attachments/assets/5d5db329-f80c-4355-99a0-b24203cd33b5" />

1. no worries, I'll just log in (we're authenticated by google, so I'll choose that)

1. clicking that opens claude.ai, which opens a standard "Sign in with google"

1. Completing that triggers a "Your organization requires SSO authentication"

<img width="417" height="425" alt="Image" src="https://github.com/user-attachments/assets/dc18569d-2eec-4264-a574-741b405e7264" />

1. no SSO mentioned before, no clickable path here except continuing with email (which doesn't seem promising).

Claude Model

Sonnet (default)

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

2.1.281

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This is not #61882 because it starts authenticated across three surfaces (web, desktop app, and CLI) and proceeds to trash them all like a drunk at a middle-child's birthday (Looking at you, Brad)

Confirm also it doesn't match #89812

Confirming it doesn't match #55268 since it doesn't get to success, it just un-auths the world.

If you got this far, thanks for reading, and accepting my strange humour. You're more awesome than people tell you.