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I've used Alpine pretty heavily but did not run into any hassle aside from "oh yeah forgot to install this package".

Could you go into more detail about the challenges one could encounter when using Alpine?

Alpine uses a different C standard library called musl compared to most well known distros that use glibc. You can run into issues if the application makes use of functions in glibc that musl has not implemented. Usually you run into them in applications that are written in C, such as in some Python modules that utilise C under the hood or in databases etc.

"I can't find $SOFTWARE in $PACKAGE_MANAGER now I have to compile it from source and my life sucks" has happened with me way more times with Alpine than Debian.

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