[GR-18163] Prefer OpenSSL 3.0, then OpenSSL 3.x, then OpenSSL 1.1

PullRequest: truffleruby/4395

lib/truffle/truffle/openssl-prefix.rb

@@ -8,10 +8,16 @@
 # GNU General Public License version 2, or
 # GNU Lesser General Public License version 2.1.
 
-# Set OPENSSL_PREFIX in ENV to find the OpenSSL headers
+# From https://openssl-library.org/policies/releasestrat/index.html
+# 3.0 is LTS, 3.1+ is non-LTS and 1.1 is EOL
 
+# See the existing formula at https://github.com/Homebrew/homebrew-core/tree/master/Formula/o
 search_homebrew = -> homebrew {
-  if prefix = "#{homebrew}/opt/[email protected]" and Dir.exist?(prefix)
+  if prefix = "#{homebrew}/opt/[email protected]" and Dir.exist?(prefix)
+    prefix
+  elsif prefix = "#{homebrew}/opt/openssl@3" and Dir.exist?(prefix)
+    prefix
+  elsif prefix = "#{homebrew}/opt/[email protected]" and Dir.exist?(prefix)
     prefix
   elsif prefix = "#{homebrew}/opt/openssl" and Dir.exist?(prefix)
     prefix
@@ -26,17 +32,20 @@
     homebrew = `brew --prefix 2>/dev/null`.strip
     homebrew = nil unless $?.success? and !homebrew.empty? and Dir.exist?(homebrew)
 
+    # See https://ports.macports.org/search/?q=openssl&name=on for the list of MacPorts openssl ports
     if homebrew and prefix = search_homebrew.call(homebrew)
       # found
-    elsif Dir.exist?('/opt/local/libexec/openssl11') # MacPorts, prefer OpenSSL 1.1 as known to be compatible
+    elsif Dir.exist?('/opt/local/libexec/openssl3')
+      prefix = '/opt/local/libexec/openssl3'
+    elsif Dir.exist?('/opt/local/libexec/openssl11')
       prefix = '/opt/local/libexec/openssl11'
-    # MacPorts, try the generic version, too, but might not be compatible
-    elsif Dir.exist?('/opt/local/include/openssl')
+    elsif Dir.exist?('/opt/local/include/openssl') # symlinks, unknown version
       prefix = '/opt/local'
     end
   end
 
   if prefix
+    # Set OPENSSL_PREFIX in ENV to find the OpenSSL headers
     ENV['OPENSSL_PREFIX'] = prefix
   else
     abort 'Could not find OpenSSL headers, install via Homebrew or MacPorts or set OPENSSL_PREFIX'