PIP was throwing warnings about needing to be updated. I made the mistake of upgrading it source ~/oprint/bin/activate pip install --upgrade pip Now the errors went away, and whenever I try to install some plugins, I an warned about depreciating of Python. DEPRECATION: Python 2.7 reached the end of its life on January 1st, 2020. Please upgrade your Python as Python 2.7 is no longer maintained. pip 21.0 will drop support for Python 2.7 in January 2021. More details about Python 2 support in pip can be found at https://pip.pypa.io/en/latest/development/release-process/#python-2-support pip 21.0 will remove support for this functionality. I've since learned that I am unable to install any plugins to octoprint. I am guessing I have to start all over again to flash my factory SD image. Which really sucks ! Does anyone have any SAFE steps to take to try and get the Robo R2 up to some level of upgraded / updated s/w?