From 88c91163cd41eb6743bff21546ce83a6c421531d Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Johannes=20M=C3=BCller?= <straightshoota@gmail.com>
Date: Sun, 10 Nov 2024 20:58:05 +0100
Subject: [PATCH 1/2] [CI] Add tests for LibreSSL 2.7

---
 .github/workflows/openssl.yml | 2 ++
 1 file changed, 2 insertions(+)

diff --git a/.github/workflows/openssl.yml b/.github/workflows/openssl.yml
index 611413e7e678..50aea38d2139 100644
--- a/.github/workflows/openssl.yml
+++ b/.github/workflows/openssl.yml
@@ -23,6 +23,8 @@ jobs:
             repository: http://dl-cdn.alpinelinux.org/alpine/v3.17/main
           - pkg: "openssl-dev=~3.3"
             repository: http://dl-cdn.alpinelinux.org/alpine/v3.20/main
+          - pkg: "libressl-dev=~2.7"
+            repository: http://dl-cdn.alpinelinux.org/alpine/v3.9/main
           - pkg: "libressl-dev=~3.4"
             repository: http://dl-cdn.alpinelinux.org/alpine/v3.15/community
           - pkg: "libressl-dev=~3.5"

From fb6a759f0096dc2b15b1b4dc58974e238724791c Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Johannes=20M=C3=BCller?= <straightshoota@gmail.com>
Date: Sun, 10 Nov 2024 21:07:32 +0100
Subject: [PATCH 2/2] Ignore errors and validate installed version

---
 .github/workflows/openssl.yml | 16 +++++++++++++---
 1 file changed, 13 insertions(+), 3 deletions(-)

diff --git a/.github/workflows/openssl.yml b/.github/workflows/openssl.yml
index 50aea38d2139..5449f39963ac 100644
--- a/.github/workflows/openssl.yml
+++ b/.github/workflows/openssl.yml
@@ -37,8 +37,18 @@ jobs:
       - name: Uninstall openssl and conflicts
         run: apk del openssl-dev openssl-libs-static libxml2-static
       - name: Install ${{ matrix.pkg }}
-        run: apk add "${{ matrix.pkg }}" --repository=${{ matrix.repository }}
-      - name: Print LibSSL version
-        run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
+        # `apk add` may exit with a failure status due to some file incompatibilities,
+        # but still install all the necessary parts for our purposes. So we ignore failure.
+        # Reason: ERROR: libressl2.7-libcrypto-2.7.5-r0: trying to overwrite etc/ssl/openssl.cnf owned by libcrypto3-3.3.2-r0.
+        run: apk add "${{ matrix.pkg }}" --repository=${{ matrix.repository }} || true
+      - name: Check LibSSL version
+        run: |
+          bin/crystal eval <<CRYSTAL
+          require "openssl"
+          p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION
+          restriction = "${{ matrix.pkg}}".partition("=~")[2]
+          version = "${{ matrix.pkg }}".starts_with?("openssl") ? LibSSL::OPENSSL_VERSION : LibSSL::LIBRESSL_VERSION
+          exit version.starts_with?(restriction) ? 0 : 1
+          CRYSTAL
       - name: Run OpenSSL specs
         run: bin/crystal spec --order=random spec/std/openssl/