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Upgrading pip system-wide should be a task for the system package manager, and doing it through pip itself seems to be frowned upon (not to mention leaving the end user with a broken package installer and broken packages). It also seems to have some fun/nasty side effects (like setting pip up to install packages for python3 instead of python2, for which pip2 is used). Debian-packaged pip, while being older, doesn't seem to break stuff for now. End user should be able to upgrade to a newer pip locally (which seems like the right thing to do), but a possibility of having a more recent pip should be looked into nonetheless.