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Rake uses glob and has for years (see @698a54980ef0e7f84447ee67f865366f56f2857a) so I think this comes from the glob changes in Ruby 2.2 since I don't see or remember rake changes to FileList resolution.
To check, does latest rake behave the same on Ruby 2.1? This way we can determine where the regression lies.
(See the ruby 2.2 ChangeLog for the glob changes on case insensitive filesystems)
The default OS X file system is case-aware, and casing used to be respected in FileList.
Including only files starting with an upper case character in gems is a very common use case which should have continued support by Rake.
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