Repeated "Authentication failed" in desktop app session panel behind TLS-inspecting corporate proxy
Description:
The Claude desktop app's session panel repeatedly shows "Authentication failed — Sign in again to continue" roughly every 5 minutes, making it unusable for extended work sessions. I have to create new sessions repeatedly to work around it.
Environment: macOS (Darwin 25.6.0), Claude desktop app, corporate network with Zscaler TLS inspection (Zscaler re-signs all TLS certs for claude.ai/api.anthropic.com/console.anthropic.com with its own CA, which is trusted in the system keychain).
Diagnosis so far:
curl/openssl s_clientagainstclaude.ai,api.anthropic.com,console.anthropic.comsucceed and verify fine against the Zscaler-issued certs (the Zscaler root CA is trusted in the macOS system keychain).- Running Claude Code via the terminal CLI in the same network does not show this issue.
- This suggests the desktop app's session/auth-refresh connection may use certificate pinning stricter than the OS trust store, which rejects the Zscaler-reissued cert even though the OS and CLI both trust it.
Request: Please have the desktop app honor the OS-level certificate trust store for its auth/session connections (or provide a way to trust an enterprise CA), consistent with how the CLI already behaves.
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