Python versioning is a critical aspect of maintaining a consistent ecosystem of packages, yet it can be challenging to get right. In this talk, we will explore the difficulties of Python versioning, including the need for upper bounds, and discuss mitigation strategies such as lockfiles in the Python packaging ecosystem (pip, poetry, and conda / mamba). We will also highlight a new community effort to analyze Python libraries dynamically and statically to detect the symbols (or libraries) they are using. By analyzing symbol usage, we can predict when package combinations will start breaking with each other, achieving a high rate of correct predictions. Our goal is to gather more community inputs to create a robust compatibility matrix. Additionally, we are doing similar work in C/C++ using libabigail to address ABI problems.