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• I found one real issue in Homebrew’s Ruby flags
Homebrew was launching Ruby with --disable=gems,rubyopt, which can break fiddle. I patched that to just --disable=rubyopt, and the patch did apply.
• That patch was not enough
Even after the flag fix, brew upgrade still fails on fiddle.
• Plain Ruby can load fiddle, but Homebrew’s Ruby environment cannot
This is the big clue. The raw Ruby binary works, but brew ruby -e 'require "fiddle"' fails.
• Why that probably happens
In Ruby 4, fiddle is no longer available the way Homebrew expects by default. So Homebrew’s Ruby 4 environment likely needs fiddle explicitly available as a gem or package in the Nix-managed Ruby environment.
• Best current conclusion
This is no longer just a simple patching problem. The remaining issue appears to be a deeper compatibility problem between:
• Homebrew 5.1.0
• Ruby 4
• and the Ruby environment provided through nix-homebrew
• Bottom line
I got far enough to prove the issue is real and isolate where it lives, but the remaining fix is advanced enough that it probably needs someone more experienced with Nix, Ruby packaging, or Homebrew internals.
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[WIP] Just bumping the homebrew version to the latest. Initial brew upgrade fails, but subsequent ones succeed.