OpenSSL/'maybe_unused' issues installing Ruby 3.0.7 on MacOS Sequoia v 15.2

[shawnacscott]

Hello!

I am trying to install a legacy Ruby 3.0.7 project on a Mac running Sequoia 15.2 on an M4 pro chip. I've tried a whole bunch of things with no success, so any guidance is very much appreciated! I've attempted to include as much information as possible in hopes something here is helpful.

When I attempt to install 3.0.7, this is the output I receive:

rbenv install 3.0.7
==> Downloading openssl-1.1.1w.tar.gz...
-> curl -q -fL -o openssl-1.1.1w.tar.gz https://dqw8nmjcqpjn7.cloudfront.net/cf3098950cb4d853ad95c0841f1f9c6d3dc102dccfcacd521d93925208b76ac8
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 9661k  100 9661k    0     0  9129k      0  0:00:01  0:00:01 --:--:-- 9131k
/var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110224622.48538.1PNTGV/openssl-1.1.1w
==> Installing openssl-1.1.1w...
-> ./config "--prefix=$HOME/.rbenv/versions/3.0.7/openssl" "--openssldir=$HOME/.rbenv/versions/3.0.7/openssl/ssl" --libdir=lib zlib-dynamic no-ssl3 shared
-> make -j 14
-> make install_sw install_ssldirs
==> Installed openssl-1.1.1w to /Users/shawnascott/.rbenv/versions/3.0.7
==> Downloading ruby-3.0.7.tar.gz...
-> curl -q -fL -o ruby-3.0.7.tar.gz https://cache.ruby-lang.org/pub/ruby/3.0/ruby-3.0.7.tar.gz
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 20.2M  100 20.2M    0     0  5782k      0  0:00:03  0:00:03 --:--:-- 5782k
/var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110224622.48538.1PNTGV/ruby-3.0.7
==> Installing ruby-3.0.7...

WARNING: ruby-3.0.7 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: using readline from homebrew
ruby-build: using libyaml from homebrew
ruby-build: using gmp from homebrew
-> ./configure "--prefix=$HOME/.rbenv/versions/3.0.7" "--with-openssl-dir=$HOME/.rbenv/versions/3.0.7/openssl" --enable-shared --with-readline-dir=/usr/local/opt/readline --with-libyaml-dir=/usr/local/opt/libyaml --with-gmp-dir=/usr/local/opt/gmp --with-ext=openssl,psych,+
-> make -j 14

BUILD FAILED (macOS 15.2 on arm64 using ruby-build 20241225.2)

You can inspect the build directory at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110224622.48538.1PNTGV
See the full build log at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110224622.48538.log

ruby-build.20250110224622.48538.log

While troubleshooting, I explored these suggestions most closely:

• `rbenv install 3.0.4` fails on macOS 13.3.1 #2185 (comment)
• Facing issues while installing ruby 2.3.7 in macOS 14.7 on x86_64 using ruby-build 20241225.2 #2492 (comment)

The suggestions in the later post seemed most promising, but when following the first step of installing rbenv's custom [email protected] tap, the tap file appears to be unavailable:

brew install rbenv/tap/[email protected]
==> Auto-updating Homebrew...
Adjust how often this is run with HOMEBREW_AUTO_UPDATE_SECS or disable with
HOMEBREW_NO_AUTO_UPDATE. Hide these hints with HOMEBREW_NO_ENV_HINTS (see `man brew`).
==> Downloading https://ghcr.io/v2/rbenv/tap/openssl/1.1/manifests/1.1.1w-1
Already downloaded: /Users/shawnascott/Library/Caches/Homebrew/downloads/cf7f86356b0cf073f13cc10544d22df72904f9fbbb879b93013d7f0c032a1ac2--openssl@1.1-1.1.1w-1.bottle_manifest.json
==> Downloading https://ghcr.io/v2/rbenv/tap/openssl/1.1/manifests/1.1.1w-1
############################################################################################################################################## 100.0%
==> Fetching rbenv/tap/[email protected]
==> Downloading https://ghcr.io/v2/rbenv/tap/openssl/1.1/blobs/sha256:eb5c26b540c5a5543edd3557d1628ce03f03e6c5ac1b219be9b34e436b10ba64
curl: (56) The requested URL returned error: 404                                                                                                     

Error: [email protected]: Failed to download resource "[email protected]"
Download failed: https://ghcr.io/v2/rbenv/tap/openssl/1.1/blobs/sha256:eb5c26b540c5a5543edd3557d1628ce03f03e6c5ac1b219be9b34e436b10ba64

However, when I run brew --prefix [email protected], it returns a result, so I decided to try step 2 anyway:

rbenv install 3.0.7 -- --with-openssl-dir="$(brew --prefix [email protected])"
==> Downloading ruby-3.0.7.tar.gz...
-> curl -q -fL -o ruby-3.0.7.tar.gz https://cache.ruby-lang.org/pub/ruby/3.0/ruby-3.0.7.tar.gz
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 20.2M  100 20.2M    0     0   9.9M      0  0:00:02  0:00:02 --:--:--  9.9M
/var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225319.15965.TiTnQi/ruby-3.0.7
==> Installing ruby-3.0.7...

WARNING: ruby-3.0.7 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: using readline from homebrew
ruby-build: using libyaml from homebrew
ruby-build: using gmp from homebrew
-> ./configure "--prefix=$HOME/.rbenv/versions/3.0.7" --with-openssl-dir=/usr/local/opt/[email protected] --enable-shared --with-readline-dir=/usr/local/opt/readline --with-libyaml-dir=/usr/local/opt/libyaml --with-gmp-dir=/usr/local/opt/gmp --with-ext=openssl,psych,+
-> make -j 14

BUILD FAILED (macOS 15.2 on arm64 using ruby-build 20241225.2)

You can inspect the build directory at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225319.15965.TiTnQi
See the full build log at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225319.15965.log

ruby-build.20250110225319.15965.log

I also tried combining that second step with the Ruby patch from the first discussion I linked, with a different error but still no luck:

cat ruby-3.0.x.patch | rbenv install --patch 3.0.7 -- --with-openssl-dir="$(brew --prefix [email protected])"
==> Downloading ruby-3.0.7.tar.gz...
-> curl -q -fL -o ruby-3.0.7.tar.gz https://cache.ruby-lang.org/pub/ruby/3.0/ruby-3.0.7.tar.gz
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 20.2M  100 20.2M    0     0  7912k      0  0:00:02  0:00:02 --:--:-- 7912k
/var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225616.44912.PRnrsx/ruby-3.0.7
==> Installing ruby-3.0.7...
-> patch -p0 --force -i "$TMPDIR/ruby-patch.RkdYsm"
patching file 'ext/bigdecimal/bigdecimal.c'

WARNING: ruby-3.0.7 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: using readline from homebrew
ruby-build: using libyaml from homebrew
ruby-build: using gmp from homebrew
-> ./configure "--prefix=$HOME/.rbenv/versions/3.0.7" --with-openssl-dir=/usr/local/opt/[email protected] --enable-shared --with-readline-dir=/usr/local/opt/readline --with-libyaml-dir=/usr/local/opt/libyaml --with-gmp-dir=/usr/local/opt/gmp --with-ext=openssl,psych,+
-> make -j 14

BUILD FAILED (macOS 15.2 on arm64 using ruby-build 20241225.2)

You can inspect the build directory at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225616.44912.PRnrsx
See the full build log at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225616.44912.log

ruby-build.20250110225616.44912.log

I also vaguely tried using gcc to compile Ruby, as suggested in one of the threads I read, but it seemed to still be invoking [email protected] somehow, so I'm not sure I invoked it all correctly:

brew install gcc
export CC=gcc
rbenv install 3.0.7
==> Downloading https://formulae.brew.sh/api/formula.jws.json
############################################################################################################################################## 100.0%
==> Downloading https://formulae.brew.sh/api/cask.jws.json
############################################################################################################################################## 100.0%
Warning: gcc 14.2.0_1 is already installed and up-to-date.
To reinstall 14.2.0_1, run:
  brew reinstall gcc
==> Downloading openssl-1.1.1w.tar.gz...
-> curl -q -fL -o openssl-1.1.1w.tar.gz https://dqw8nmjcqpjn7.cloudfront.net/cf3098950cb4d853ad95c0841f1f9c6d3dc102dccfcacd521d93925208b76ac8
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 9661k  100 9661k    0     0  8588k      0  0:00:01  0:00:01 --:--:-- 8588k
/var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225928.79716.BinbqK/openssl-1.1.1w
==> Installing openssl-1.1.1w...
-> ./config "--prefix=$HOME/.rbenv/versions/3.0.7/openssl" "--openssldir=$HOME/.rbenv/versions/3.0.7/openssl/ssl" --libdir=lib zlib-dynamic no-ssl3 shared
-> make -j 14
-> make install_sw install_ssldirs
==> Installed openssl-1.1.1w to /Users/shawnascott/.rbenv/versions/3.0.7
==> Downloading ruby-3.0.7.tar.gz...
-> curl -q -fL -o ruby-3.0.7.tar.gz https://cache.ruby-lang.org/pub/ruby/3.0/ruby-3.0.7.tar.gz
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 20.2M  100 20.2M    0     0  3251k      0  0:00:06  0:00:06 --:--:-- 3750k
/var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225928.79716.BinbqK/ruby-3.0.7
==> Installing ruby-3.0.7...

WARNING: ruby-3.0.7 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: using readline from homebrew
ruby-build: using libyaml from homebrew
ruby-build: using gmp from homebrew
-> ./configure "--prefix=$HOME/.rbenv/versions/3.0.7" "--with-openssl-dir=$HOME/.rbenv/versions/3.0.7/openssl" --enable-shared --with-readline-dir=/usr/local/opt/readline --with-libyaml-dir=/usr/local/opt/libyaml --with-gmp-dir=/usr/local/opt/gmp --with-ext=openssl,psych,+
-> make -j 14

BUILD FAILED (macOS 15.2 on arm64 using ruby-build 20241225.2)

You can inspect the build directory at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225928.79716.BinbqK
See the full build log at /var/folders/lt/xsbgf3sx15qb467wft_h22qh0000gn/T/ruby-build.20250110225928.79716.log

ruby-build.20250110225928.79716.log

If you've made it this far, thanks for reading and for any suggestions you may have on what I can try next, or any additional information I could provide that would be helpful!

[mislav]

The suggestions in the later post seemed most promising, but when following the first step of installing rbenv's custom [email protected] tap, the tap file appears to be unavailable

That's my bad; I was messing around with tap “bottles” yesterday. If you try it again after brew update, it should work (please let me know if it does!), or you can force it to compile from source (which should only be necessary as a last resort):

brew install --build-from-source rbenv/tap/[email protected]

I also tried combining that second step with the Ruby patch from the first discussion I linked, with a different error but still no luck:

You're getting closer! I do think the patch is necessary to get around the error in bigdecimal, so keep doing that, but I think now you're hitting another issue: the fact that your Homebrew installation has been migrated from an Intel machine and is currently in the /usr/local prefix, when it should be in /opt/homebrew which is standard for M* chipsets. Use an online guide on how to migrate your Homebrew installation, which likely involves saving a list of all installed formula, nuking your old Homebrew installation, and reinstalling all formula in the new location.

[shawnacscott]

Thank you so much for your thorough and speedy reply! These two things were indeed my issue!

So, TL;DR for anyone reading later, after fixing my Homebrew install, these are the steps that allowed install of Ruby 3.0.7 on my Apple Silicon M4 Pro chip Mac running Sequoia 15.2:

• Running brew install rbenv/tap/[email protected] (From the rbenv homebrew tap README)
• Downloading the Ruby 3.0.7 big decimal patch to a local file called ruby-3.0.x.patch
• Running cat ruby-3.0.x.patch | rbenv install --patch 3.0.7 -- --with-openssl-dir="$(brew --prefix [email protected])" which applies the patch file and uses the older [email protected] library to compile Ruby.

For anyone else who finds they have either a migrated old Homebrew install, or like me it turns out, half an install for intel and half for silicon, I did something akin to:

• alias oldbrew=/usr/local/bin/brew
• oldbrew list (you could do something fancier, but I just copied and pasted the output somewhere I could refer to it later)
• Used the Homebrew uninstall instructions for a specific path like curl -fsSLO https://raw.githubusercontent.com/Homebrew/install/HEAD/uninstall.sh /bin/bash uninstall.sh --path /usr/local
• Used the Homebrew install instructions to reinstall in the correct Apple Silicon location, which you can confirm by running brew --prefix, which should output /opt/homebrew for Apple Silicon.
• Manually reinstalled any packages I needed