Problems building 2.7.x on M1 Monterey (12.6.2) Intel architecture

[lowell-lewis]

We have a legacy project running on 2.7.3 but this problem creeped up recently with our setup process on M1 macs. We install most of the dependencies with Intel brew including rbenv and ruby-build. The build was working fine with openssl 1.1.1q and prior builds of ruby-build. More recent attempts resulted in build failures with openssl 1.1.1s and the latest ruby-build. We have to install Intel brew in a non-standard prefix (/usr/local/homebrew) b/c of security restrictions on our corporate laptops. The build error is below. It's looking in the wrong location for the openssl lib. We observe the error despite specifying the openssl directory when trying to install it. This worked fine previously so not sure what introduced it but seems related to the ruby-build and openssl upgrades.

RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix [email protected])" rbenv install 2.7.7.

generating x86_64-darwin21-fake.rb
x86_64-darwin21-fake.rb updated
./miniruby -I./lib -I. -I.ext/common  ./tool/runruby.rb --extout=.ext  -- --disable-gems -r./x86_64-darwin21-fake ./tool/rbinstall.rb --make="make" --dest-dir="" --extout=".ext" --mflags="" --make-flags="" --data-mode=0644 --prog-mode=0755 --installed-list .installed.list --mantype="doc" --rdoc-output=".ext/rdoc" --html-output=".ext/html"
/private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require': dlopen(/private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/.ext/x86_64-darwin21/openssl.bundle, 0x0009): Library not loaded: '/usr/local/opt/[email protected]/lib/libssl.1.1.dylib' (LoadError)
  Referenced from: '/private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/.ext/x86_64-darwin21/openssl.bundle'
  Reason: tried: '/usr/local/opt/[email protected]/lib/libssl.1.1.dylib' (no such file), '/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/libssl.1.1.dylib' (no such file), '/private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/libssl.1.1.dylib' (no such file) - /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/.ext/x86_64-darwin21/openssl.bundle
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/.ext/common/openssl.rb:13:in `<top (required)>'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/security.rb:12:in `<top (required)>'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/package.rb:44:in `<top (required)>'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/installer.rb:11:in `<top (required)>'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from /private/var/folders/2z/wcjkhr9d7m9dnlfylqhr874h0000gp/T/ruby-build.20230118204700.7466.PVzaug/ruby-2.7.7/lib/rubygems/core_ext/kernel_require.rb:83:in `require'
	from ./tool/rbinstall.rb:713:in `<module:RbInstall>'
	from ./tool/rbinstall.rb:649:in `<main>'
make: *** [do-install-all] Error 1

[mislav]

1. What is the output of brew --prefix [email protected]? It seems like it is /usr/local/opt/[email protected], but should it be /usr/local/homebrew/opt/[email protected] because of your nonstandard Homebrew install location?
2. Can you check /usr/local/opt/[email protected]/lib to see if there is anything there?

[lowell-lewis]

Yeah, brew --prefix reports the correct value of /usr/local/homebrew/opt/[email protected]. My opt directory is actually /usr/local/homebrew/opt and the dynamic lib the build process is looking for is there. I'm just not sure why it is not honoring the configure option we specify when triggering the build from rbenv. Our current workaround is to symlink /usr/local/homebrew/opt to /usr/local/opt and /usr/local/homebrew/Cellar to /usr/local/Cellar and run spctl --global-disable to get past the Mac security policy and that works but none of that was necessary before the openssl upgrade to 1.1.1s and ruby-build.