diff --git a/.azure-pipelines/ci.yml b/.azure-pipelines/ci.yml
index 0fe754bb071ea3..835a728d1340ef 100644
--- a/.azure-pipelines/ci.yml
+++ b/.azure-pipelines/ci.yml
@@ -57,7 +57,7 @@ jobs:
   variables:
     testRunTitle: '$(build.sourceBranchName)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.1k
+    openssl_version: 3.0.0-alpha14
 
   steps:
   - template: ./posix-steps.yml
@@ -83,7 +83,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1k
+    openssl_version: 3.0.0-alpha14
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.azure-pipelines/pr.yml b/.azure-pipelines/pr.yml
index 2d32e6d49bcc0e..9d09837b5d0390 100644
--- a/.azure-pipelines/pr.yml
+++ b/.azure-pipelines/pr.yml
@@ -57,7 +57,7 @@ jobs:
   variables:
     testRunTitle: '$(system.pullRequest.TargetBranch)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.1k
+    openssl_version: 3.0.0-alpha14
 
   steps:
   - template: ./posix-steps.yml
@@ -83,7 +83,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1k
+    openssl_version: 3.0.0-alpha14
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 39c349bf6e910b..8f6db3f5e69649 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -126,12 +126,22 @@ jobs:
       run: make buildbottest TESTOPTS="-j4 -uall,-cpu"
 
   build_ubuntu:
-    name: 'Ubuntu'
+    name: 'Ubuntu ${{ matrix.openssl_ver }}'
     runs-on: ubuntu-20.04
     needs: check_source
     if: needs.check_source.outputs.run_tests == 'true'
+    strategy:
+      fail-fast: false
+      matrix:
+        openssl_ver: [1.1.1k, 3.0.0-alpha14]
+        include:
+        - openssl_ver: 1.1.1k
+          testmode: 'full'
     env:
-      OPENSSL_VER: 1.1.1k
+      OPENSSL_VER: ${{ matrix.openssl_ver }}
+      MULTISSL_DIR: ${{ github.workspace }}/multissl
+      OPENSSL_DIR: ${{ github.workspace }}/multissl/openssl/${{ matrix.openssl_ver }}
+      LD_LIBRARY_PATH: ${{ github.workspace }}/multissl/openssl/${{ matrix.openssl_ver }}/lib
     steps:
     - uses: actions/checkout@v2
     - name: Register gcc problem matcher
@@ -146,12 +156,16 @@ jobs:
         key: ${{ runner.os }}-multissl-openssl-${{ env.OPENSSL_VER }}
     - name: Install OpenSSL
       if: steps.cache-openssl.outputs.cache-hit != 'true'
-      run: python3 Tools/ssl/multissltests.py --steps=library --base-directory $PWD/multissl --openssl $OPENSSL_VER --system Linux
+      run: python3 Tools/ssl/multissltests.py --steps=library --base-directory $MULTISSL_DIR --openssl $OPENSSL_VER --system Linux
     - name: Configure CPython
-      run: ./configure --with-pydebug --with-openssl=$PWD/multissl/openssl/$OPENSSL_VER
+      run: ./configure --with-pydebug --with-openssl=$OPENSSL_DIR
     - name: Build CPython
       run: make -j4
     - name: Display build info
       run: make pythoninfo
     - name: Tests
       run: xvfb-run make buildbottest TESTOPTS="-j4 -uall,-cpu"
+      if: ${{ matrix.testmode == 'full' }}
+    - name: SSL tests
+      run: ./python Lib/test/ssltests.py
+      if: ${{ matrix.testmode != 'full' }}
diff --git a/.github/workflows/coverage.yml b/.github/workflows/coverage.yml
index d8d932a7652d15..4152050e312097 100644
--- a/.github/workflows/coverage.yml
+++ b/.github/workflows/coverage.yml
@@ -25,7 +25,7 @@ jobs:
     name: 'Ubuntu (Coverage)'
     runs-on: ubuntu-latest
     env:
-      OPENSSL_VER: 1.1.1k
+      OPENSSL_VER: 3.0.0-alpha14
     steps:
     - uses: actions/checkout@v2
     - name: Install Dependencies
diff --git a/.travis.yml b/.travis.yml
index fc063216914446..1581eba384de90 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -10,7 +10,7 @@ cache:
 
 env:
   global:
-    - OPENSSL=1.1.1k
+    - OPENSSL=3.0.0-alpha14
     - OPENSSL_DIR="$HOME/multissl/openssl/${OPENSSL}"
     - PATH="${OPENSSL_DIR}/bin:$PATH"
     - CFLAGS="-I${OPENSSL_DIR}/include"
diff --git a/Mac/BuildScript/build-installer.py b/Mac/BuildScript/build-installer.py
index 25a6a24f564947..733c0ad2b4bef5 100755
--- a/Mac/BuildScript/build-installer.py
+++ b/Mac/BuildScript/build-installer.py
@@ -242,9 +242,9 @@ def library_recipes():
 
     result.extend([
           dict(
-              name="OpenSSL 1.1.1k",
-              url="https://www.openssl.org/source/openssl-1.1.1k.tar.gz",
-              checksum='c4e7d95f782b08116afa27b30393dd27',
+              name="OpenSSL 3.0.0-alpha14",
+              url="https://www.openssl.org/source/openssl-3.0.0-alpha14.tar.gz",
+              checksum='65bbd34991af56f0d94139c42dd40001',
               buildrecipe=build_universal_openssl,
               configure=None,
               install=None,