asdf install ruby latest installing outdated openssl version, failing

[mgibson323]

Steps to reproduce the behavior

On MacOS 13.4.1 (ARM64) with asdf installed via brew, and openssl version 3.1.2, attempt to install ruby latest

$ asdf version
v0.12.0

$ openssl version
OpenSSL 3.1.2 1 Aug 2023 (Library: OpenSSL 3.1.2 1 Aug 2023)

$ asdf install ruby latest

The installation fails with other ruby versions besides latest, as well.

I suspect the openssl version is causing my installation to fail.

Note: I am not very familiar with Ruby or using these tools, but I want to install it to use it for some other tools I need for work. I was directed to this repo by this comment.

Expected vs. actual behavior

Expected: ISBAT install Ruby using asdf so I can use a different version aside from the MacOS default.
Actual: Installation via asdf fails

Logs

$ asdf install ruby latest
To follow progress, use 'tail -f /var/folders/89/vrmgx5c91fl4dbdf_ydq2y4w0000gn/T/ruby-build.20230804125921.3441.log' or pass --verbose
Downloading openssl-3.1.1.tar.gz...
-> https://dqw8nmjcqpjn7.cloudfront.net/b3aa61334233b852b63ddb048df181177c2c659eb9d4376008118f9c08d07674
Installing openssl-3.1.1...

BUILD FAILED (macOS 13.4.1 using ruby-build 20230717)

Inspect or clean up the working tree at /var/folders/89/vrmgx5c91fl4dbdf_ydq2y4w0000gn/T/ruby-build.20230804125921.3441.YNnJS2
Results logged to /var/folders/89/vrmgx5c91fl4dbdf_ydq2y4w0000gn/T/ruby-build.20230804125921.3441.log

Last 10 log lines:
  "_main", referenced from:
     implicit entry/start for main executable
  "_test_info", referenced from:
      _test_cha_cha_internal in chacha_internal_test-bin-chacha_internal_test.o
  "_test_uchar_eq", referenced from:
      _test_cha_cha_internal in chacha_internal_test-bin-chacha_internal_test.o
ld: symbol(s) not found for architecture arm64
clang: error: linker command failed with exit code 1 (use -v to see invocation)
make[1]: *** [test/chacha_internal_test] Error 1
make: *** [build_sw] Error 2

[mgibson323]

additional info:

$ asdf info
OS:
Darwin gitlab.local 22.5.0 Darwin Kernel Version 22.5.0: Thu Jun  8 22:22:20 PDT 2023; root:xnu-8796.121.3~7/RELEASE_ARM64_T6000 arm64

SHELL:
zsh 5.9 (x86_64-apple-darwin22.0)

BASH VERSION:
5.2.15(1)-release

ASDF VERSION:
v0.12.0

ASDF INTERNAL VARIABLES:
ASDF_DEFAULT_TOOL_VERSIONS_FILENAME=.tool-versions
ASDF_DATA_DIR=/Users/<user>/.asdf
ASDF_DIR=/opt/homebrew/Cellar/asdf/0.12.0/libexec
ASDF_CONFIG_FILE=/Users/<user>/.asdfrc

ASDF INSTALLED PLUGINS:
ruby                         https://github.com/asdf-vm/asdf-ruby.git master 8cb9721

[mislav]

I have no idea what is causing this failure, but you could avoid having to compile OpenSSL by linking to an existing one.

You could install an OpenSSL version with Homebrew, which is generally faster due to Homebrew's precompiled bottles: brew install openssl@1.1

Then you can instruct ruby-build to link to that:

RUBY_CONFIGURE_OPTS="--disable-install-doc --with-openssl-dir=$(brew --prefix openssl@1.1)"

[mgibson323]

Thanks! That makes sense, my apologies for noob-ness.

The installation is now failing differently, so I am not sure if it makes sense to keep this open.

$ RUBY_CONFIGURE_OPTS="--disable-install-doc --with-openssl-dir=$(brew --prefix openssl@3)" asdf install ruby latest
To follow progress, use 'tail -f /var/folders/89/vrmgx5c91fl4dbdf_ydq2y4w0000gn/T/ruby-build.20230809124226.49767.log' or pass --verbose
Downloading ruby-3.2.2.tar.gz...
-> https://cache.ruby-lang.org/pub/ruby/3.2/ruby-3.2.2.tar.gz
Installing ruby-3.2.2...
ruby-build: using readline from homebrew
ruby-build: using libyaml from homebrew
ruby-build: using gmp from homebrew

BUILD FAILED (macOS 13.5 using ruby-build 20230717)

Inspect or clean up the working tree at /var/folders/89/vrmgx5c91fl4dbdf_ydq2y4w0000gn/T/ruby-build.20230809124226.49767.XbjUD4
Results logged to /var/folders/89/vrmgx5c91fl4dbdf_ydq2y4w0000gn/T/ruby-build.20230809124226.49767.log

Last 10 log lines:
compiling digest.c
compiling date_core.c
linking shared-object coverage.bundle
compiling date_parse.c
compiling date_strftime.c
compiling date_strptime.c
linking shared-object digest.bundle
linking shared-object -test-/string.bundle
linking shared-object date_core.bundle
make: *** [build-ext] Error 2

I can open a different issue or I can share more from the log here, please let me know which is appropriate.

Thank you!

[mislav]

You can share more of the log file here; thank you. You can also paste the whole thing as a gist link, if you cannot isolate the error message yourself.

I wonder if the Ruby compilation problem is somehow related to openssl compilation problem. As a precaution, make sure that your Homebrew installation wasn't set up in amd64 compatibility mode (some people did this with their M1 machines because either Homebrew or various software wasn't compatible with arm64) and that you since forgot about it. I don't know how exactly to check for this, however. You can start with type brew to rule out the possibility that brew is a shell alias for something else.

[mgibson323]

Thanks!

I did initially have Brew set up for amd64 compatibility, but I've since used this method to switch it all to arm64.

Here is the gist containing the full log: https://gist.github.com/mgibson323/6b295a5f346f49d8f3c696edad755fa6

[mislav]

@mgibson323 This error coming from bigdecimal sounds familiar:

./missing.h:139:1: error: static declaration of 'rb_rational_den' follows non-static declaration

Here is the Ruby bug report. I don't know why you now experience this with a much newer Ruby version, nor what causes the original issue. One person reports that linking Homebrew's coreutils formula into your PATH may be the culprit. For more information, you can inspect ext/bigdecimal/mkmf.log in your build directory.

[jwalinrami]

@mgibson323 @mislav Please ignore my report above as I was able to resolve the issue with help from our mgr who knows Ruby well and here is what we did,

1. Uninstall and Reinstall Xcode and Xcode command line tools (14.3.1)

2. Set .zprofile file as below

---

eval "$(/opt/homebrew/bin/brew shellenv)"

export RUBY_CONFIGURE_OPTS="--with-libyaml-dir=$(brew --prefix libyaml) --with-openssl-dir=$(brew --prefix openssl@3) --disable-install-doc"

export PATH="/opt/homebrew/opt/openssl@3/bin:$PATH"
export LDFLAGS="-L/opt/homebrew/opt/openssl@3/lib $LDFLAGS"
export CPPFLAGS="-I/opt/homebrew/opt/openssl@3/include $CPPFLAGS"
export PKG_CONFIG_PATH="/opt/homebrew/opt/openssl@3/lib/pkgconfig"

---

3. Set .zshrc file as below

---

. /opt/homebrew/opt/asdf/libexec/asdf.sh

---

4. Installed different (older) version just to make sure there are no issues with latest version by running below, which succeeded and did not even try to download openssl this time

asdf install ruby 3.1.1

5. Installed latest version by running below, which succeeded

asdf install ruby 3.2.2

[mislav]

Thanks for the update. BTW you only need to set up RUBY_CONFIGURE_OPTS in your environment to link to Homebrew's openssl, but you don't need to edit PATH, LDFLAGS, CPPFLAFS, nor PKG_CONFIG_PATH. You may remove all those settings from your environment, as they will affect all compilation of programs unrelated to Ruby in the future.