@dgelessus, this is not an important question to me at least right now. But from what I can see pip in stash is only aware of modules it's installed. So 'pip update sympy' fails as it's not aware it's installed. But it would seems to me that stash could know the pre installed Libs and do the update to the correct directory. I know little about this, but that is what comes to mind. I can also imagine a Pythonista app/uiView using the Stash API to present a list of installed packages with version numbers and a update (update to version) button same as they do in PyCharm.
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