Tried to gradually upgrade projects written Ruby and Python, that were not touched in 10 years. The dependencies were based on C extensions that depended on libs not existing anymore. It was even impossible to get the original version compiled, because in was dependent on a Linux distro version that doesn't exist anymore, even as docker images.
That was the hard lesson: depending on dynamically loaded libs means you need to constantly maintain the project and even if it has no visible bugs, or doesn't depend on the code having security vulnerabilities, you need to adapt it to evolve together with the libs, and that is needed even if you actually use only what's "old" in the libs. But we're not saving every megabyte of a disk space anymore like in 90s. Switching to static compilation does wonders for maintainability.