rbenv Ruby 3.0.6 "cannot load such file -- socket"

[roloand]

I'm on a new Mac: M5 Pro, OS Tahoe 26.4. Installed rbenv fresh, and installed ruby 3.0.6 with it, using a patch as outlined in other threads. For the record, these are the commands I used:

brew install rbenv/tap/openssl@1.1
brew link --overwrite openssl@1.1
curl -fsSL https://github.com/ruby/ruby/commit/1dfe75b0beb7171b8154ff0856d5149be0207724.patch | rbenv install 3.0.6 --patch

Ruby 3.0.6 is installed successfully. However, when trying gem install bundler or just try to do anything, I get the following error (including stack trace that comes up when I try bundle install):

<internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require': cannot load such file -- socket (LoadError)
        from <internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/net/protocol.rb:22:in `<top (required)>'
        from <internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
from <internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/net/http.rb:23:in `<top (required)>'
from <internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
        from <internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/vendor/net-http-persistent/lib/net/http/persistent.rb:1:in `<top (required)>'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/vendored_persistent.rb:11:in `require_relative'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/vendored_persistent.rb:11:in `<top (required)>'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/fetcher.rb:3:in `require_relative'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/fetcher.rb:3:in `<top (required)>'
        from <internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
from <internal:/Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/cli/install.rb:48:in `run'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/cli.rb:253:in `block in install'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/settings.rb:131:in `temporary'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/cli.rb:252:in `install'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/vendor/thor/lib/thor/command.rb:27:in `run'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/vendor/thor/lib/thor/invocation.rb:127:in `invoke_command'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/vendor/thor/lib/thor.rb:392:in `dispatch'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/cli.rb:31:in `dispatch'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/vendor/thor/lib/thor/base.rb:485:in `start'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/cli.rb:25:in `start'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/gems/3.0.0/gems/bundler-2.2.33/libexec/bundle:49:in `block in <top (required)>'
from /Users/username/.rbenv/versions/3.0.6/lib/ruby/3.0.0/bundler/friendly_errors.rb:103:in `with_friendly_errors'
        from /Users/username/.rbenv/versions/3.0.6/lib/ruby/gems/3.0.0/gems/bundler-2.2.33/libexec/bundle:37:in `<top (required)>'
from /Users/username/.rbenv/versions/3.0.6/bin/bundle:23:in `load'
        from /Users/username/.rbenv/versions/3.0.6/bin/bundle:23:in `<main>'

I tried installing and using 3.1.0 on a separate directory and installing bundler and I'm getting the same error. I also ran the rbenv_doctor script and it didn't diagnose any issues. I'd appreciate any help with this, as I've been at it by myself for a whole day. Thanks!

[mislav]

Hi, since this is not a bug with rbenv, but a build failure in Ruby's own build system, I've converted this to a Discussion in the ruby-build repository.

First of all, I can reproduce this on macOS 26.2 when attempting to install both Ruby 3.0.6 and the latest 3.0.x version, Ruby 3.0.7:

$ curl -fsSL https://github.com/ruby/ruby/commit/1dfe75b0beb7171b8154ff0856d5149be0207724.patch | \
  rbenv install 3.0 --force --keep --patch -- --with-ext=socket,+

Some notes:

• --force makes it so that rbenv will try to re-install the Ruby version even if one exists already (but has broken socket extension);
• --keep keeps the original Ruby source tree on disk even after a successful build so you can inspect individual log files (normally only the main build log is kept, but that one doesn't always contain all the information);
• --with-ext=socket,+ passed as a ruby configure flag will ensure that the overall build fails if the "socket" extension fails to build (without that, the build would succeed, but network-related Ruby functionality would not work).

I get this output:

*** Following extensions are not compiled:
gdbm:
        Could not be configured. It will not be installed.
        Check /Users/mislav/.rbenv/sources/3.0.7/ruby-3.0.7/ext/gdbm/mkmf.log for more details.
socket:
        Could not be configured. It will not be installed.
        /Users/mislav/.rbenv/sources/3.0.7/ruby-3.0.7/ext/socket/extconf.rb:660: No such file or directory @ rb_sysopen - /usr/include/netinet6/in6.h
        Check /Users/mislav/.rbenv/sources/3.0.7/ruby-3.0.7/ext/socket/mkmf.log for more details.

BUILD FAILED (macOS 26.2 on arm64 using ruby-build 20260512)

You can inspect the build directory at /Users/mislav/.rbenv/sources/3.0.7
See the full build log at /var/folders/6k/fwzzx67n163b0lfftyw3313h0000gn/T/ruby-build.20260515165014.31269.log

We can see that "socket" extension failed to compile, and now the build is properly aborted. The reason why the extension failed to compile might be in the extension's own log, which I'm uploading here: https://gist.github.com/mislav/46a5082b48f42938e41632f4f165b9c9

This log file is hard to read because it contains everything that Ruby attempted to test during "socket" extension compilation, and that may include warnings and errors that were non-fatal. In fact, by casually scanning this log file I can't detect what exactly is the cause of the error, but I know for a fact that Ruby 3.0 was able to compile using an older version of macOS. This might be an example of an issue that stems from newer macOS changing some of its libraries and APIs, and older Rubies become incompatible with the OS due to their EoL (End-of-Life) status. You may be able to find another patch to apply to this Ruby version, but instead I'd strongly advise you to upgrade your project to a Ruby version that compiles on your system.

Finally, do NOT do brew link --overwrite openssl@1.1 on your system. You might have seen it suggested as a workaround by the community, but later on it can cause more harm to your other software than it benefits here. Run brew unlink openssl@1.1 to fix.

[mislav]

The RString problem seems to have been fixed in Ruby 3.2, but I'm not clear on whether that patch applies cleanly to Ruby 3.0. (It looks to me like it doesn't.) You may have more luck if you start investigating from here: ruby/ruby@357d601

[roloand]

@mislav thanks for the info, I really appreciate it. I'll take a look at the link provided. I did try with Ruby 3.2 afterwards and that installation worked well. If I can't find anything else that could be a fix for this, I'll have to upgrade. Thanks again!