What is the problem?
When I look at the software update tab, it shows a yellow dialog box that says "this version of the python environmane is not supported for direct updates."
Python 2.7.9 (you have 2.7.9)
pip 9.0.1 (you have 8.1.1)
setuptools 5.5.1 (you have 5.5.1)
What did you already try to solve it?
Read through Pip 19.0.3 NOT installing? and saw that you shouldn't upgrade pip manually. Now I'm wondering if I need to reinstall OctoPi or if there's another way to get octoprint to update pip.
Additional information about your setup
OctoPi 0.13.0
I'm not sure if there are problems jumping from an older version up until the recent. Unless you are instructed to upgrade your pip by someone who knows better, I wouldn't. (And yet, that might be the fix.)
I'm noting @foosel since she would know if there is something that can easily be done... while I research the forum for past advice.
If it were me, I'd buy another microSD card, set it up with the new OctoPi image, re-install my plugins, upload my gcode and call it a day.
The problem here is less pip and more that the general environment is a fairly ancient OctoPi 0.13.0. Create a backup, flash a new image version on a new SD card (because these things also wear out...) and restore the backup.
