Issue #19115 has been updated by thomthom (Thomas Thomassen). I built Ruby 3.1.2 that we use in our product with this patch applied, and it worked on our systems. Would be nice to see it backported. ---------------------------------------- Bug #19115: RubyGems fails to detect OpenSSL in --with-static-linked-ext builds https://bugs.ruby-lang.org/issues/19115#change-100995 * Author: thomthom (Thomas Thomassen) * Status: Closed * Priority: Normal * ruby -v: 3.1.2, 3.2.0dev * Backport: 2.7: UNKNOWN, 3.0: UNKNOWN, 3.1: UNKNOWN ---------------------------------------- Related discussion: https://bugs.ruby-lang.org/issues/18876 We are seeing OpenSSL failing to autoload with the Ruby build we've been using. (We first observed this when using `Gem.install` that relies on autoload of OpenSSL). Our last working build was Ruby 2.7.2 with similar config. This causes RubyGems' `HAVE_OPENSSL` constant to be incorrectly initialized, and subsequent calls to `Gem.install` fails. There might be other scenarios that fail as a result of that, but we've not managed to identified that. ``` module Gem HAVE_OPENSSL = defined? OpenSSL::SSL # :nodoc: ``` Our Ruby 3.1.2 config: ``` '--prefix=/Users/user/.conan/data/ruby/3.1.2/sketchup/stable/build/bd95825b99dcb274d0e577fbdc953653a9ea0fb9' '--with-openssl-dir=/Users/user/.conan/data/openssl/1.1.1q/sketchup/stable/package/93ae0b0e7eebe0611c04d3e0d9bbf49fbce92332' '--with-libyaml-dir=/Users/user/.conan/data/libyaml/0.2.5/sketchup/stable/package/a56a950abed2e10dbdc26845400f0a034d97c454' '--disable-install-doc' '--disable-install-rdoc' '--enable-shared' '--enable-load-relative' '--with-static-linked-ext' '--without-debug' '--without-gdbm' '--without-gettext' '--without-irb' '--without-mkmf' '--without-rdoc' '--without-readline' '--without-tk' '--bindir=${prefix}/bin' '--sbindir=${prefix}/bin' '--libexecdir=${prefix}/bin' '--libdir=${prefix}/lib' '--includedir=${prefix}/include' '--oldincludedir=${prefix}/include' '--datarootdir=${prefix}/share' 'cflags=-mmacosx-version-min=10.14 -fdeclspec' 'cxxflags=-mmacosx-version-min=10.14 -fdeclspec' 'LDFLAGS=-mmacosx-version-min=10.14 -fdeclspec' ``` We also tested with latest build from master (November 8th 2022): ``` ./ruby -ve 'p RbConfig::CONFIG["configure_args"]' ruby 3.2.0dev (2022-11-07T19:35:21Z master b14f133054) [x86_64-darwin20] " '--prefix=/Users/vmehta/ruby/ruby-master/' '--with-openssl-dir=/Users/vmehta/.conan/data/openssl/1.1.1q/sketchup/stable/package/f2d937af1fa19d5fc4095849a65d1927e9e75ae7/' '--with-libyaml-dir=/Users/vmehta/.conan/data/libyaml/0.2.5/sketchup/stable/package/3fc084e254210603a5c5aece184b2d45e2509b30' '--disable-install-doc' '--disable-install-rdoc' '--enable-shared' '--enable-load-relative' '--with-static-linked-ext' '--without-debug' '--without-gdbm' '--without-gettext' '--without-irb' '--without-mkmf' '--without-rdoc' '--without-readline' '--without-tk'" ``` Using an RVM of Ruby 3.1.2 this appear to work as expected. But using out configuration, that we've used for the Ruby 2.x versions are now failing. We haven't been able to figure out the reason for this. -- https://bugs.ruby-lang.org/