Steve Dower <steve.do...@python.org> added the comment:

You probably need to also select the "Install for All Users" checkbox, rather 
than just updating the target path. Running as admin *technically* gives you 
the ability to write to those locations, but it also implies that nobody except 
Admin should be able to access it. Choosing the proper option should do it 
correctly.

This kind of issue can also arise when you directly delete the install, rather 
than uninstalling it. Best thing to do if you can is to run a repair through 
the Add Remove Programs entry, and then uninstall it (this is because ensurepip 
needs a working install to uninstall itself... not ideal, but that's how it was 
added). Then you should be able to do the proper install.

However, if it was previously installed for All Users, then switching the 
option in your new install might be able to handle it. Trying to upgrade from 
per-user to all users seems to hit issues sometimes.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue45420>
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