deerbox: first-run auth fails with 401 until deer runs first

[KakkoiDev]

Description

Fresh install of deer + deerbox (same install.sh run). Running deerbox first results in a 401 authentication error. Running deer (TUI) first succeeds. After that, deerbox works too.

No macOS Keychain access dialog was shown in either case.

Reproduction

1. Fresh install via curl -fsSL https://raw.githubusercontent.com/zdavison/deer/main/install.sh | bash
2. Run deerbox in a repo - auth fails with 401
3. Run deer in same repo - auth succeeds
4. Run deerbox again - auth succeeds

Environment

• macOS (Darwin 24.5.0, arm64)
• Credentials stored in macOS Keychain under Claude Code-credentials
• No ~/.claude/agent-oauth-token file, no CLAUDE_CODE_OAUTH_TOKEN env var

Analysis

Both binaries use security find-generic-password -s "Claude Code-credentials" -w to read the Keychain. Possible causes:

• Cold-start race in Bun's subprocess spawning of security
• Keychain access grant is shared between the two binaries (same codesign/install), but requires one successful access before the other works

[zdavison]

Thanks for the report, I'll investigate.

[KakkoiDev]

Possibly related: I hit a similar first-run failure with deerbox after a self-update (v0.8.1 -> v0.9.4). The auth proxy subprocess timed out instead of returning a 401, but the pattern is the same - first run after update fails, second run works fine.

user@MM202408-05 deer % deerbox
warn: ignoring extra certs from /Applications/Zscaler/cert/ZscalerRootCertificate-2048-SHA256.crt, load failed: error:10000009:SSL routines:OPENSSL_internal:PEM routines
deerbox: updating v0.8.1 → v0.9.4...
deerbox: updated to v0.9.4, restarting...
  Creating worktree...
  Preparing ecosystems: bun
  [bun] Prepopulating node_modules...
  Starting sandbox...
Fatal: auth-proxy subprocess did not become ready in 10s
user@MM202408-05 deer % deer
warn: ignoring extra certs from /Applications/Zscaler/cert/ZscalerRootCertificate-2048-SHA256.crt, load failed: error:10000009:SSL routines:OPENSSL_internal:PEM routines
deer: updating v0.8.1 → v0.9.4...
deer: updated to v0.9.4, restarting...
user@MM202408-05 deer %

The shared trigger may be the self-update restart path. Both failures (401 auth and proxy timeout) happen on the first run when the binary self-updates and restarts. On the second run there's no update/restart step, and everything works.

• macOS Darwin 24.5.0, arm64
• Zscaler SSL inspection active (cert warning in output)
• No CLAUDE_CODE_OAUTH_TOKEN env var, credentials from Keychain