When system-wide pip turns out too old (e.g. for lacking support for pip check), one may end up trying to update pip using a command like:

sudo pip install --upgrade pip

That's likely to end up with this message:

Not uninstalling pip at /usr/lib/python2.7/dist-packages, owned by OS

That non-error and the confusion that easily happens right after is why I'm writing this post. So let's look at the whole thing in a bit more context on a shell, a Debian jessie one in this case:

# cat /etc/debian_version 
8.10

# pip install --upgrade pip ; echo $?
Downloading/unpacking pip from https://pypi.python.org/packages/b6[..]44
  Downloading pip-9.0.1-py2.py3-none-any.whl (1.3MB): 1.3MB downloaded
Installing collected packages: pip
  Found existing installation: pip 1.5.6
    Not uninstalling pip at /usr/lib/python2.7/dist-packages, owned by OS
Successfully installed pip
Cleaning up...
0

# pip --version
pip 1.5.6 from /usr/lib/python2.7/dist-packages (python 2.7)

Now the interesting part is that it looks like pip would not have been updated. That impression is false : Latest pip has been installed successfully (to /usr/local/bin). One of two things is going on here: a) Unexpected Path resolution order You have /usr/bin/ before /usr/local/bin/ in $PATH, e.g. as with root of Debian jessie, so that the new pip has no chance of winning the race of path resolution for pip. For example:

# sed 's,:,\n,g' <<<"$PATH"
/bin
/sbin
/usr/bin
/usr/sbin
/usr/local/bin
/usr/local/sbin
/opt/bin
/usr/lib/llvm/5/bin
/usr/lib/llvm/4/bin

b) Location hashing at shell level Your shell has hashed the old location of pip (as Bash would do) and "hides" the new version from you in the current shell session. To see that in action, we utilize Bash builtins type and hash:

# type pip
pip is hashed (/usr/bin/pip)

# pip --version
pip 1.5.6 from /usr/lib/python2.7/dist-packages (python 2.7)

# hash -d pip

# type pip
pip is /usr/local/bin/pip

# pip --version
pip 9.0.1 from /usr/local/lib/python2.7/dist-packages (python 2.7)

So in either case you can run a recent pip from /usr/local/bin/pip right after pip install --upgrade pip, no need to resort to get-pip.py or so, in fact.