diff --git a/.github/workflows/ci-macvim.yaml b/.github/workflows/ci-macvim.yaml
index d8a61db404..ac0b48dee6 100644
--- a/.github/workflows/ci-macvim.yaml
+++ b/.github/workflows/ci-macvim.yaml
@@ -12,18 +12,22 @@ concurrency:
   cancel-in-progress: true
 
 env:
-  MACOSX_DEPLOYMENT_TARGET: '10.9'
+  MACOSX_DEPLOYMENT_TARGET: '10.13'
+  MACOSX_DEPLOYMENT_TARGET_LEGACY: '10.9'
+
+  MACVIM_ARCHS: "x86_64 arm64"  # Universal app for Intel/Apple Silicon
+  MACVIM_ARCHS_LEGACY: "x86_64" # Legacy builds only need to build x86-64 because Apple Silicon can't run on these old OSes
 
   CC: clang
 
-  VERSIONER_PERL_VERSION: '5.18'
+  VERSIONER_PERL_VERSION: '5.30'
   VERSIONER_PYTHON_VERSION: '2.7'
   vi_cv_path_python: /usr/local/bin/python
   vi_cv_path_python3: /usr/local/bin/python3
   vi_cv_path_plain_lua: /usr/local/bin/lua
   vi_cv_path_ruby: /usr/local/opt/ruby/bin/ruby
-  vi_cv_dll_name_perl: /System/Library/Perl/5.18/darwin-thread-multi-2level/CORE/libperl.dylib
-  vi_cv_dll_name_python: /usr/local/Library/Frameworks/Python.framework/Versions/2.7/Python
+  vi_cv_dll_name_perl: /System/Library/Perl/5.30/darwin-thread-multi-2level/CORE/libperl.dylib
+  vi_cv_dll_name_python: /usr/local/Frameworks/Python.framework/Versions/2.7/Python
   vi_cv_dll_name_python3: /usr/local/Frameworks/Python.framework/Versions/3.10/Python # Make sure to keep src/MacVim/vimrc synced with the Python version here for the Python DLL detection logic.
   vi_cv_dll_name_python3_arm64: /opt/homebrew/Frameworks/Python.framework/Versions/3.10/Python
   vi_cv_dll_name_ruby: /usr/local/opt/ruby/lib/libruby.dylib
@@ -40,16 +44,26 @@ jobs:
   # Builds and test MacVim
   build-and-test:
 
-    # Test on macOS 11.x / 12.x, and also older version of Xcode for compatibility testing.
+    # Test on macOS 11.x / 12.x, and also older versions of Xcode for compatibility testing.
     strategy:
       fail-fast: false
       matrix:
         include:
-          - os: macos-11
-            publish: true
+          # Oldest version of Xcode supported on GitHub Action to test source code backwards compatibility
           - os: macos-11
             xcode: '11.7'
+
+          # Older version of Xcode, and used to publish legacy builds (for macOS 10.9 - 10.12)
+          - os: macos-12
+            xcode: '14.0' # last version of Xcode that uses the macOS 12 SDK, which still supports deploying to macOS 10.9
+            publish: true
+            legacy: true
+            publish_postfix: '_10.9'
+
+          # Most up to date OS and Xcode. Used to publish release for the main build.
           - os: macos-12
+            xcode: '14.1'
+            publish: true
 
     runs-on: ${{ matrix.os }}
 
@@ -57,6 +71,12 @@ jobs:
       - name: Checkout
         uses: actions/checkout@v3
 
+      - name: Set up legacy build
+        if: matrix.legacy
+        run: |
+          echo "MACOSX_DEPLOYMENT_TARGET=$MACOSX_DEPLOYMENT_TARGET_LEGACY" >> $GITHUB_ENV
+          echo "MACVIM_ARCHS=$MACVIM_ARCHS_LEGACY" >> $GITHUB_ENV
+
       # Set up, install, and cache gettext library for localization.
       #
       # Instead of using the default binary installed by Homebrew, need to build our own because gettext is statically
@@ -93,9 +113,16 @@ jobs:
         env:
           HOMEBREW_NO_AUTO_UPDATE: 1
         run: |
-          brew install python
+          brew install python3
           brew install ruby
           brew install lua
+
+          # CI sometimes have custom installed Python instead of using Homebrew. Forcefully re-
+          # link Python, and then check that we are using the Homebrew version. This avoids us
+          # using a mystery Python installation that we don't control.
+          brew unlink python3 && brew link --overwrite python3
+          readlink -f $vi_cv_path_python3 | grep "^$(brew --cellar python3)"
+
           if [[ -d /usr/local/Cellar/perl ]]; then
             # We just use system perl to reduce dependencies
             brew unlink perl
@@ -129,7 +156,7 @@ jobs:
               --enable-rubyinterp=dynamic
               --enable-luainterp=dynamic
               --with-lua-prefix=/usr/local
-              --with-macarchs="x86_64 arm64"
+              --with-macarchs="$MACVIM_ARCHS"
             )
           else
             CONFOPT+=(
@@ -215,8 +242,8 @@ jobs:
           # Smoketest scripting languages
           macvim_excmd -c 'lua print("Test")'
           macvim_excmd -c 'perl VIM::Msg("Test")'
-          macvim_excmd -c 'py import sys; print("Test")'
-          macvim_excmd -c 'py3 import sys; print("Test")'
+          macvim_excmd -c 'py print "Test"'
+          macvim_excmd -c 'py3 print("Test")'
           macvim_excmd -c 'ruby puts("Test")'
 
           # Check that localized messages work by printing ':version' and checking against localized word
@@ -231,8 +258,10 @@ jobs:
           # Make sure we are building universal x86_64 / arm64 builds and didn't accidentally create a thin app.
           check_arch() {
             local archs=($(lipo -archs "$1"))
-            if [[ ${archs[@]} != "x86_64 arm64" ]]; then
+            if [[ ${archs[@]} != "$MACVIM_ARCHS" ]]; then
               echo "Wrong arch(s) in $1: ${archs[@]}"; false
+            else
+              lipo -info "$1"
             fi
           }
           check_arch "${VIM_BIN}"
@@ -258,9 +287,13 @@ jobs:
           # CI environment.
           make -C src macvim-dmg CREATEDMG_FLAGS=--skip-jenkins
 
+          if ${{ matrix.publish_postfix != '' }}; then
+            mv src/MacVim/build/Release/MacVim.dmg src/MacVim/build/Release/MacVim${{ matrix.publish_postfix }}.dmg
+          fi
+
       - name: Upload MacVim image
         if: startsWith(github.ref, 'refs/tags/') && matrix.publish
         uses: actions/upload-artifact@v3
         with:
-          name: MacVim.dmg
-          path: src/MacVim/build/Release/MacVim.dmg
+          name: MacVim${{ matrix.publish_postfix  }}.dmg
+          path: src/MacVim/build/Release/MacVim${{ matrix.publish_postfix }}.dmg