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POK-94: detect/handle LibreSSL / legacy TLS to prevent opaque gateway handshake failures#35

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saheljalal merged 1 commit into
mainfrom
pok-94-detect-libressl-legacy-tls
Jul 3, 2026
Merged

POK-94: detect/handle LibreSSL / legacy TLS to prevent opaque gateway handshake failures#35
saheljalal merged 1 commit into
mainfrom
pok-94-detect-libressl-legacy-tls

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Summary

  • Add a Python TLS preflight to gateway HTTP clients (gateway on, models, verify, doctor reachability) that detects LibreSSL and OpenSSL < 1.1.1 before attempting HTTPS
  • Surface an actionable error (e.g. brew install python@3.12 on macOS) instead of the opaque SSLV3_ALERT_HANDSHAKE_FAILURE
  • Add a Python TLS check to aikit doctor prerequisites
  • Translate remaining TLS handshake failures into the same actionable message

Test plan

  • Unit tests for version parsing (LibreSSL, OpenSSL 1.0.x/1.1.1+/3.x, unknown)
  • Preflight blocks network when TLS is legacy
  • SSLError handshake failure maps to actionable hint
  • Full gateway test suite passes on OpenSSL 3.x Linux

Closes POK-94

Add a TLS preflight to gateway HTTP clients and aikit doctor so macOS system
Python and other legacy OpenSSL builds get an actionable fix instead of an
opaque SSLV3_ALERT_HANDSHAKE_FAILURE.

Co-authored-by: Cursor <cursoragent@cursor.com>
Co-authored-by: multica-agent <github@multica.ai>
@saheljalal saheljalal merged commit 39e6cc9 into main Jul 3, 2026
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@saheljalal saheljalal deleted the pok-94-detect-libressl-legacy-tls branch July 3, 2026 08:31
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