Martin v. Löwis added the comment: I don't think the installer needs fixing beyond fixing mimetypes. If ensurepip fails, the whole installation ought to fail (IMO); that's the way MSI is supposed to work. It's the same if some other component could not be installed for some reason (permissions, out of disk space, etc): the entire installation gets rolled back. So I disagree with Steve that it would be desirable to let pip installation fail silently.
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