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SSL: RECORD_LAYER_FAILURE when downloading template on macOS #1461

@G-lalala

Description

@G-lalala

Environment

  • OS: macOS 15.6.1 (Darwin 24.6.0)
  • Python: 3.14.2 (installed via Homebrew)
  • OpenSSL: 3.6.0
  • specify-cli: v0.0.22
  • Installation method: uv tool install specify-cli --from git+https://github.com/github/spec-kit.git

Description

specify init fails with an SSL/TLS handshake error when attempting to download the template ZIP file from release-assets.githubusercontent.com.

Command

specify init . --ai claude --force --ignore-agent-tools
Image

Questions

  1. Has anyone else encountered this issue on macOS with recent OpenSSL versions?
  2. Are there any known compatibility issues with release-assets.githubusercontent.com and OpenSSL 3.6.0?
  3. Would it be possible to provide an alternative download method (e.g., direct GitHub API asset download without redirect)?

What Works ✅

What Fails ❌

  • Download from https://release-assets.githubusercontent.com/... (after redirect from GitHub releases)
  • Using --skip-tls flag does not resolve the issue
  • Both Python's urllib and httpx (with truststore) fail with the same error
  • System curl (LibreSSL 3.3.6) also fails with: error:1404B42E:SSL routines:ST_CONNECT:tlsv1 alert protocol version

Thanks.

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