[BUG] Can't use Claude Cowork via personal subscription on DEP enrolled Macs

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?

I am trying to use Claude Cowork via personal account on my office provided Mac. This used to work quite well in early April. Either the desktop app made changes OR my employer's MDM policy changed.

Cowork on a DEP/MDM-enrolled corporate Mac is fundamentally broken until either Anthropic fixes the EKU fields in ephemeral cert generation, or IT relaxes policy. c=Cert generation issue on managed Macs; the ephemeral CA should generate certs with proper EKU fields

2026-05-12 22:30:25.512354-0700 0x2be2a5 Default 0x0 75325 0 Claude: (CoreAnalytics) [com.apple.CoreAnalytics:client] Entering exit handler.
2026-05-12 22:30:25.512357-0700 0x2be2a5 Default 0x0 75325 0 Claude: (CoreAnalytics) [com.apple.CoreAnalytics:client] Queueing exit procedure onto XPC queue. Any further messages sent will be discarded. activeSendTransactions=0
2026-05-12 22:30:25.512392-0700 0x2be2a5 Default 0x0 75325 0 Claude: (CoreAnalytics) [com.apple.CoreAnalytics:client] Exiting exit handler.
2026-05-12 22:30:29.031437-0700 0x2b75e5 Default 0x0 75325 0 Claude: (CoreAnalytics) [com.apple.CoreAnalytics:client] Entering exit handler.
2026-05-12 22:30:29.031438-0700 0x2b75e5 Default 0x0 75325 0 Claude: (CoreAnalytics) [com.apple.CoreAnalytics:client] Queueing exit procedure onto XPC queue. Any further messages sent will be discarded. activeSendTransactions=0
2026-05-12 22:30:29.031460-0700 0x2b75e5 Default 0x0 75325 0 Claude: (CoreAnalytics) [com.apple.CoreAnalytics:client] Exiting exit handler.
2026-05-12 22:30:35.931373-0700 0x2be950 Activity 0xc8ea1e 78900 0 Claude: (libsystem_info.dylib) Retrieve Group by ID
2026-05-12 22:30:41.703137-0700 0x2be923 Activity 0xc8f553 78900 0 Claude: (TCC) TCCAccessRequest() IPC
2026-05-12 22:30:44.071379-0700 0x2be92f Default 0xc8f555 78900 0 Claude: (Security) [com.apple.securityd:SecError] [leaf ExtendedKeyUsage]
2026-05-12 22:35:04.141375-0700 0x2be923 Default 0x0 78900 0 Claude: (libxpc.dylib) [com.apple.xpc:connection] [0x13400069e20] activating connection: mach=false listener=false peer=false name=(anonymous)

What Should Happen?

Claude cowork on desktop app should work with personal account credentials on employer provided macs

Error Messages/Logs

Invalid API

Steps to Reproduce

Enroll mac into DEP / MDM
Try using cowork from a personal subscription - not corporate

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

Not sure - early April version

Claude Code Version

Claude 1.7196.0 (2dbd78) 2026-05-12T05:34:40.000Z

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Label: area:cowork platform:macos bug