But if the libraries and extensions are not maintaining compatibility, you need to freeze your dependencies, and sometimes that means freezing the dependencies

But if the libraries and extensions are not maintaining compatibility, you need to freeze your dependencies, and sometimes that means freezing the dependencies of your dependencies, or even your OS, and then you hope your machine doesn't break. It's not a tragedy, backwards-compatibility is a burden, and I understand maintainers, especially volunteers not wanting to do it. But migration is a pain, I found the conversion was not too hard, but testing the migrated scripts for breakage was time consuming. FYI, the cause of my latest migration was that the latest version for the mysql-connector for python no longer works with 2.7. See the changelog entry for v8.0.24 here: https://github.com/mysql/mysql-connector-python/blob/master/CHANGES.txt https://github.com/mysql/mysql-connector-python/blob/master/... So something to consider if you want to stay on Python 2 forever.