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chore: Upgrade ruby to 3.4.4 #2219

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@mroderick mroderick commented Jul 12, 2025

This PR breaks on my local machine when using bin/dup.

Posting it as a draft to get some 👀 eyes on it from an expert.

I tried following the example from the previous ruby upgrade, and think I've done the same things, but this branc is failing when running bin/dup.

rake aborted!
LoadError: libruby.so.3.2: cannot open shared object file: No such file or directory - /usr/local/bundle/gems/msgpack-1.7.5/lib/msgpack/msgpack.so (LoadError)
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
/usr/local/bundle/gems/msgpack-1.7.5/lib/msgpack.rb:7:in '<top (required)>'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache/store.rb:5:in 'block in <top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/explicit_require.rb:50:in 'Bootsnap::ExplicitRequire.with_gems'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache/store.rb:5:in '<top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache.rb:77:in 'Kernel#require_relative'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache.rb:77:in '<top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap.rb:5:in 'Kernel#require_relative'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap.rb:5:in '<top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/setup.rb:3:in 'Kernel#require_relative'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/setup.rb:3:in '<top (required)>'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
/planner/config/boot.rb:5:in '<top (required)>'
/planner/config/application.rb:1:in 'Kernel#require_relative'
/planner/config/application.rb:1:in '<top (required)>'
/planner/rakefile:4:in 'Kernel#require_relative'
/planner/rakefile:4:in '<top (required)>'

Caused by:
LoadError: libruby.so.3.2: cannot open shared object file: No such file or directory - /usr/local/bundle/gems/msgpack-1.7.5/lib/msgpack/msgpack.so (LoadError)
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
/usr/local/bundle/gems/msgpack-1.7.5/lib/msgpack.rb:7:in '<top (required)>'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache/store.rb:5:in 'block in <top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/explicit_require.rb:47:in 'Bootsnap::ExplicitRequire.with_gems'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache/store.rb:5:in '<top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache.rb:77:in 'Kernel#require_relative'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/load_path_cache.rb:77:in '<top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap.rb:5:in 'Kernel#require_relative'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap.rb:5:in '<top (required)>'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/setup.rb:3:in 'Kernel#require_relative'
/usr/local/bundle/gems/bootsnap-1.18.4/lib/bootsnap/setup.rb:3:in '<top (required)>'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
<internal:/usr/local/lib/ruby/3.4.0/rubygems/core_ext/kernel_require.rb>:37:in 'Kernel#require'
/planner/config/boot.rb:5:in '<top (required)>'
/planner/config/application.rb:1:in 'Kernel#require_relative'
/planner/config/application.rb:1:in '<top (required)>'
/planner/rakefile:4:in 'Kernel#require_relative'
/planner/rakefile:4:in '<top (required)>'
(See full trace by running task with --trace)

@mroderick
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Ping @olleolleolle. Can you advise on how I might complete this Ruby upgrade?

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