Sounds like pip (popular package manager for Python) avoids this problem because you don't use pip to install or upgrade itself. If using the package manager to

Sounds like pip (popular package manager for Python) avoids this problem because you don't use pip to install or upgrade itself. If using the package manager to install updated versions of itself is an intended use case, then I agree with others: it should check your path after the install and make sure the newly installed binary is the one that will get used. Otherwise the design is making it too easy to do the wrong thing.