Repeated "Authentication failed" in desktop app session panel behind TLS-inspecting corporate proxy

Status Open
Maintainer reply None cached
Activity 1 comment · opened Sep 28, 2026

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_client against claude.ai, api.anthropic.com, console.anthropic.com succeed 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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