Ever since I started using PyPy and then had it quietly work fine for years , I've been keeping it in mind as a generally easy way to speed up any Python program that could benefit from a performance boost (which programs PyPy could accelerate sometimes surprised me ). But that was in the era when most everything we had was Python 2 based. Now that I'm moving more and more things to Python 3, there's a little issue opening up that I've been thinking about. That issue is what versions of (C)Python PyPy supports, which is to say which language version it implements.
If you look at the PyPy site , you'll see that of Python 3 versions they support, the most recent one is 3.11, which the regular ('CPython') version of was released in late 2022. If you've followed a bit of PyPy development news, you may have read that the PyPy project is resource constrained and thus lags behind CPython for things like implementing language features or standard library changes. My understanding is that PyPy's timeline for implementing language features beyond 3.11 is "whenever we can but don't hold your breath".
On the one hand, Python 3.11 is a perfectly okay version of Python. On the other hand, Python 3 keeps adding more features in newer versions, including useful features. One area I've definitely noticed some changes is in type annotations and typing in general. Typing changes the code I write and I'm fairly certain that the sort of type hints that are (conveniently) available probably will do so too. And at a certain point, more and more code that I want to work with will require something more recent than Python 3.11. If I'm lucky, I'll get warnings about this; if I'm not, I'll some day discover that the reason pipx isn't upgrading various things I have installed through it is that the newer versions aren't compatible with Python 3.11.
(For all I know this is already happening. Or maybe pipx explicitly complains about this situation. Although I have some machines not using PyPy with pipx, and so far they have the same version of programs I install everywhere, such as Python LSP servers .)
In the long run I suspect that this is going to lead me to abandon my use of PyPy with pipx, and probably to step away from PyPy as Ubuntu LTS Python versions keep increasing beyond what PyPy supports. Right now, we have Ubuntu 22.04, Ubuntu 24.04, and Ubuntu 26.04 machines, which have Python 3.10, 3.12, and 3.14 respectively. PyPy's 3.11 doesn't look particularly bad (and it will be years before we stop having 22.04 machines). And of course Ubuntu 28.04 is a fairly long way away, and PyPy might increase its Python 3 version by then.
(This makes me feel a bit sad. PyPy has been good for me, and it's still a great option for Python 2, one that we may turn to sooner or later.)