diff --git a/.github/workflows/openssl.yml b/.github/workflows/openssl.yml
index 8cdb888e3621..d518c93a51de 100644
--- a/.github/workflows/openssl.yml
+++ b/.github/workflows/openssl.yml
@@ -7,95 +7,34 @@ concurrency:
   cancel-in-progress: ${{ github.ref != 'refs/heads/master' }}
 
 jobs:
-  openssl3_0:
+  libssl_test:
     runs-on: ubuntu-latest
-    name: "OpenSSL 3.0"
+    name: "${{ matrix.pkg }}"
     container: crystallang/crystal:1.13.1-alpine
+    strategy:
+      fail-fast: false
+      matrix:
+        include:
+          - pkg: "openssl1.1-compat-dev=~1.1.1"
+            repository: http://dl-cdn.alpinelinux.org/alpine/v3.18/community
+          - pkg: "openssl-dev=~3.0"
+            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=~3.4"
+            repository: http://dl-cdn.alpinelinux.org/alpine/v3.15/community
+          - pkg: "libressl-dev=~3.5"
+            repository: http://dl-cdn.alpinelinux.org/alpine/v3.16/community
+          - pkg: "libressl-dev=~3.8"
+            repository: http://dl-cdn.alpinelinux.org/alpine/v3.20/community
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v4
-      - name: Uninstall openssl
-        run: apk del openssl-dev libxml2-static
-      - name: Upgrade alpine-keys
-        run: apk upgrade alpine-keys
-      - name: Install openssl 3.0
-        run: apk add "openssl-dev=~3.0" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.17/main
-      - name: Check LibSSL version
-        run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
-      - name: Run OpenSSL specs
-        run: bin/crystal spec --order=random spec/std/openssl/
-  openssl3_3:
-    runs-on: ubuntu-latest
-    name: "OpenSSL 3.3"
-    container: crystallang/crystal:1.13.1-alpine
-    steps:
-      - name: Download Crystal source
-        uses: actions/checkout@v4
-      - name: Install openssl 3.3
-        run: apk add "openssl-dev=~3.3" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.20/community
-      - name: Check LibSSL version
-        run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
-      - name: Run OpenSSL specs
-        run: bin/crystal spec --order=random spec/std/openssl/
-  openssl111:
-    runs-on: ubuntu-latest
-    name: "OpenSSL 1.1.1"
-    container: crystallang/crystal:1.13.1-alpine
-    steps:
-      - name: Download Crystal source
-        uses: actions/checkout@v4
-      - name: Uninstall openssl
-        run: apk del openssl-dev
-      - name: Install openssl 1.1.1
-        run: apk add "openssl1.1-compat-dev=~1.1.1" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.18/community
-      - name: Check LibSSL version
-        run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
-      - name: Run OpenSSL specs
-        run: bin/crystal spec --order=random spec/std/openssl/
-  libressl34:
-    runs-on: ubuntu-latest
-    name: "LibreSSL 3.4"
-    container: crystallang/crystal:1.13.1-alpine
-    steps:
-      - name: Download Crystal source
-        uses: actions/checkout@v4
-      - name: Uninstall openssl
-        run: apk del openssl-dev openssl-libs-static
-      - name: Upgrade alpine-keys
-        run: apk upgrade alpine-keys
-      - name: Install libressl 3.4
-        run: apk add "libressl-dev=~3.4" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.15/community
-      - name: Check LibSSL version
-        run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
-      - name: Run OpenSSL specs
-        run: bin/crystal spec --order=random spec/std/openssl/
-  libressl35:
-    runs-on: ubuntu-latest
-    name: "LibreSSL 3.5"
-    container: crystallang/crystal:1.13.1-alpine
-    steps:
-      - name: Download Crystal source
-        uses: actions/checkout@v2
-      - name: Uninstall openssl
-        run: apk del openssl-dev openssl-libs-static
-      - name: Install libressl 3.5
-        run: apk add "libressl-dev=~3.5" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.16/community
-      - name: Check LibSSL version
-        run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
-      - name: Run OpenSSL specs
-        run: bin/crystal spec --order=random spec/std/openssl/
-  libressl38:
-    runs-on: ubuntu-latest
-    name: "LibreSSL 3.5"
-    container: crystallang/crystal:1.13.1-alpine
-    steps:
-      - name: Download Crystal source
-        uses: actions/checkout@v2
-      - name: Uninstall openssl
-        run: apk del openssl-dev openssl-libs-static
-      - name: Install libressl 3.8
-        run: apk add "libressl-dev=~3.8" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.20/community
-      - name: Check LibSSL version
+      - 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'
       - name: Run OpenSSL specs
         run: bin/crystal spec --order=random spec/std/openssl/