MacOS AppleSillicon (M2) build of ruby 3.2.1 runs in error

[Chief-Detektor]

Oh boy I ran into a rabit hole..
While I was trying to have a local ruby version working I came to an error which I could not really solve.
There are some discussions here that share some of the symptoms but somehow nothing could help me in my situation.

I managed to build ruby via

RUBY_CONFIGURE_OPTS="--disable-install-doc" ruby-build 3.2.1 ~/.rubies/ruby-3.2.1

but it refuses to install. The output is:

ruby-build: using openssl@3 from homebrew
==> Downloading ruby-3.2.1.tar.gz...
-> curl -q -fL -o ruby-3.2.1.tar.gz https://cache.ruby-lang.org/pub/ruby/3.2/ruby-3.2.1.tar.gz
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 19.5M  100 19.5M    0     0  33.4M      0 --:--:-- --:--:-- --:--:-- 33.6M
==> Installing ruby-3.2.1...
ruby-build: using readline from homebrew
ruby-build: using libyaml from homebrew
ruby-build: using gmp from homebrew
-> ./configure "--prefix=$HOME/.rubies/ruby-3.2.1" --with-openssl-dir=/opt/homebrew/opt/openssl@3 --enable-shared --with-readline-dir=/opt/homebrew/opt/readline --with-libyaml-dir=/opt/homebrew/opt/libyaml --with-gmp-dir=/opt/homebrew/opt/gmp --disable-install-doc
-> make -j 12
-> make install

BUILD FAILED (macOS 14.1 on arm64 using ruby-build 20231107)

You can inspect the build directory at /var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109125025.33583.meRefz
See the full build log at /var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109125025.33583.log

The error message is kind of misleading because in the folder there is a working ruby executable.
Somehow the install step is failing. But the install process creates folders and copies files into the configured prefix folder:

bin   include   lib   share

The error message with --disable-install-doc:

*** Following extensions are not compiled:
-test-/file:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/-test-/file/mkmf.log for more details.
-test-/symbol:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/-test-/symbol/mkmf.log for more details.
bigdecimal:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/bigdecimal/mkmf.log for more details.
date:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/date/mkmf.log for more details.
digest/md5:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/digest/md5/mkmf.log for more details.
digest/rmd160:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/digest/rmd160/mkmf.log for more details.
digest/sha1:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/digest/sha1/mkmf.log for more details.
digest/sha2:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/digest/sha2/mkmf.log for more details.
etc:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/etc/mkmf.log for more details.
fiddle:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/fiddle/mkmf.log for more details.
io/console:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/io/console/mkmf.log for more details.
io/nonblock:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/io/nonblock/mkmf.log for more details.
io/wait:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/io/wait/mkmf.log for more details.
json/parser:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/json/parser/mkmf.log for more details.
openssl:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/openssl/mkmf.log for more details.
pathname:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/pathname/mkmf.log for more details.
psych:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/psych/mkmf.log for more details.
pty:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/pty/mkmf.log for more details.
racc/cparse:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/racc/cparse/mkmf.log for more details.
rbconfig/sizeof:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/rbconfig/sizeof/mkmf.log for more details.
readline:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/readline/mkmf.log for more details.
socket:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/socket/mkmf.log for more details.
stringio:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/stringio/mkmf.log for more details.
strscan:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/strscan/mkmf.log for more details.
syslog:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/syslog/mkmf.log for more details.
zlib:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check ext/zlib/mkmf.log for more details.
rbs-2.8.2/ext/rbs_extension:
	Could not be configured. It will not be installed.
	/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109132121.71082.CKelwg/ruby-3.2.1/lib/mkmf.rb:490: The compiler failed to generate an executable file.
	You have to install development tools first.
	Check .bundle/gems/rbs-2.8.2/ext/rbs_extension/mkmf.log for more details.
*** Fix the problems, then remove these directories and try again if you want.

making enc
make[1]: Nothing to be done for `enc'.
making trans
make[1]: Nothing to be done for `./enc/trans'.
making encs
make[1]: Nothing to be done for `encs'.
SDKROOT= ./miniruby -I./lib -I. -I.ext/common  ./tool/runruby.rb --extout=.ext  -- --disable-gems -r./arm64-darwin23-fake ./tool/rbinstall.rb --make="make" --dest-dir="" --extout=".ext" --ext-build-dir="./ext" --mflags="" --make-flags="" --data-mode=0644 --prog-mode=0755 --installed-list .installed.list --mantype="doc"  --gnumake --install=all --exclude=doc
installing binary commands:         /Users/andre/.rbenv/versions/3.2.1/bin
installing base libraries:          /Users/andre/.rbenv/versions/3.2.1/lib
installing arch files:              /Users/andre/.rbenv/versions/3.2.1/lib/ruby/3.2.0/arm64-darwin23
installing pkgconfig data:          /Users/andre/.rbenv/versions/3.2.1/lib/pkgconfig
installing extension objects:       /Users/andre/.rbenv/versions/3.2.1/lib/ruby/3.2.0/arm64-darwin23
installing extension objects:       /Users/andre/.rbenv/versions/3.2.1/lib/ruby/site_ruby/3.2.0/arm64-darwin23
installing extension objects:       /Users/andre/.rbenv/versions/3.2.1/lib/ruby/vendor_ruby/3.2.0/arm64-darwin23
installing extension headers:       /Users/andre/.rbenv/versions/3.2.1/include/ruby-3.2.0/arm64-darwin23
installing extension scripts:       /Users/andre/.rbenv/versions/3.2.1/lib/ruby/3.2.0
installing extension scripts:       /Users/andre/.rbenv/versions/3.2.1/lib/ruby/site_ruby/3.2.0
installing extension scripts:       /Users/andre/.rbenv/versions/3.2.1/lib/ruby/vendor_ruby/3.2.0
installing extension headers:       /Users/andre/.rbenv/versions/3.2.1/include/ruby-3.2.0/ruby
installing command scripts:         /Users/andre/.rbenv/versions/3.2.1/bin
installing library scripts:         /Users/andre/.rbenv/versions/3.2.1/lib/ruby/3.2.0
installing common headers:          /Users/andre/.rbenv/versions/3.2.1/include/ruby-3.2.0
installing manpages:                /Users/andre/.rbenv/versions/3.2.1/share/man/man1
installing default gems from lib:   /Users/andre/.rbenv/versions/3.2.1/lib/ruby/gems/3.2.0
                                    abbrev 0.1.1
                                    base64 0.1.1
                                    benchmark 0.2.1
                                    bundler 2.4.6
/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/installer.rb:351:in `rescue in install': uninitialized constant Gem::Installer::Zlib (NameError)
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/installer.rb:301:in `install'
	from ./tool/rbinstall.rb:881:in `block in install'
	from ./tool/rbinstall.rb:721:in `no_write'
	from ./tool/rbinstall.rb:881:in `install'
	from ./tool/rbinstall.rb:989:in `block in install_default_gem'
	from ./tool/rbinstall.rb:976:in `each'
	from ./tool/rbinstall.rb:976:in `install_default_gem'
	from ./tool/rbinstall.rb:913:in `block in <main>'
	from ./tool/rbinstall.rb:1077:in `block in <main>'
	from ./tool/rbinstall.rb:1074:in `each'
	from ./tool/rbinstall.rb:1074:in `<main>'
<internal:/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/core_ext/kernel_require.rb>:88:in `require': cannot load such file -- psych (LoadError)
	from <internal:/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/core_ext/kernel_require.rb>:88:in `require'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems.rb:608:in `load_yaml'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/config_file.rb:346:in `load_file'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/config_file.rb:189:in `initialize'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems.rb:329:in `new'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems.rb:329:in `configuration'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/user_interaction.rb:167:in `verbose'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/installer.rb:544:in `generate_bin_script'
	from ./tool/rbinstall.rb:891:in `generate_bin_script'
	from ./tool/rbinstall.rb:855:in `generate_bin_script'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/installer.rb:506:in `block in generate_bin'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/installer.rb:490:in `each'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/installer.rb:490:in `generate_bin'
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131456.11214.DURzyA/ruby-3.2.1/lib/rubygems/installer.rb:331:in `install'
	from ./tool/rbinstall.rb:881:in `block in install'
	from ./tool/rbinstall.rb:721:in `no_write'
	from ./tool/rbinstall.rb:881:in `install'
	from ./tool/rbinstall.rb:989:in `block in install_default_gem'
	from ./tool/rbinstall.rb:976:in `each'
	from ./tool/rbinstall.rb:976:in `install_default_gem'
	from ./tool/rbinstall.rb:913:in `block in <main>'
	from ./tool/rbinstall.rb:1077:in `block in <main>'
	from ./tool/rbinstall.rb:1074:in `each'
	from ./tool/rbinstall.rb:1074:in `<main>'
make: *** [do-install-nodoc] Error 1
external command failed with status 2

and without --disable-install-doc:

Generating RDoc documentation
/private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131902.42473.hNWz2E/ruby-3.2.1/lib/rdoc/rdoc.rb:6:in `require': cannot load such file -- pathname (LoadError)
	from /private/var/folders/jb/28pcckkj1klcdmjtqcr_nw0m0000gn/T/ruby-build.20231109131902.42473.hNWz2E/ruby-3.2.1/lib/rdoc/rdoc.rb:6:in `<top (required)>'
	from ./libexec/rdoc:16:in `require'
	from ./libexec/rdoc:16:in `<main>'
make: *** [rdoc] Error 1
external command failed with status 2

I assume that somehow the extensions are not compiled and therefore the build cannot succeed.
What can I do now?

[mislav]

Could you try xcode-select --install?

That installs Command Line Tools on macOS, which is a prerequisite to building almost any kind of software.

[Chief-Detektor]

Hi! Yes I did this. And it responds with xcode-select: note: Command line tools are already installed. Use "Software Update" in System Settings or the softwareupdate command line interface to install updates.
Somethings is wierd here but I think it's worth taking a look in how ruby is configured and compiled for homebrew: [Formula code: ruby.rb

I will poke a bit more around maybe I find something

[Chief-Detektor]

Okay! I fixed my system. For whatever reason xcode-select was not configured to use the default path. By running sudo xcode-select -r (for reset to system default). I could restore the normal behavior.
The error occurred because the system could not link the extensions/binary properly.
RDocs are now generated as well.

Thanks for hinting me in the right direction. (Also suggesting xcode-select -r besides xcode-select install may help others in future)