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It appears that on Mac, Directory.EnumerateFiles, when called with a search pattern, behaves in a case-sensitive manner. Deep in the bowels of the Mono sources on github, it seems this may be controlled via a #define of IS_PORTABILITY_CASE and others.
As a workaround, list everything w/o a search pattern and filter yourself, if you care to have a case insensitive search occur.
Seems this has also been mentioned here:
It looks like IS_PORTABILITY_CASE is not initialised correctly. We'll probably have to read some HFS+ as it can be both case sensitive and insensitive.
The easiest workaround for you is to set MONO_IOMAP=case
Created attachment 26244 [details]
I can reproduce with Mono 184.108.40.206 (master/df33c092de3) on an case-insensitive APFS volume.
The workaround provided in https://bugzilla.xamarin.com/show_bug.cgi?id=28875#c2 do gives the expected behavior.