jp2a
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Colors not working in macOS terminal
On macOS terminal.app:
Meanwhile on Linux, the exact same pup.txt works perfectly.

Any ideas why?
Which version of jp2a are you using? The version on Homebrew is pretty old, better color support has been added in v1.0.9.
Not sure, but version mismatch wouldn't explain why the same pup.txt would look fine on Linux but not in macOS.
https://gist.github.com/dllu/bb108d8365ffba191472635f4bc32c28

According to https://github.com/termstandard/colors#not-supporting-truecolor Terminal.app does not support 24-bit truecolor, therefore pup.txt does not work. That's currently my best guess. Unfortunately I don't have a Mac so I can't debug this properly.
(jp2a should automatically use ANSI color (4-bit) if truecolor is not supported.)