I knew this Sam well, as I also had worked in the IT department during my college days.
While you present a plausible sounding explanation for his lack of knowledge about TCP tooling, networking duties were under his purview as well. He spent a lot of time on the clock not hungrily learning technology, but sneaking off to smoke weed. I watched him once pack a bowl and smoke it while driving on the highway with his knees, coming back from a remote campus. He was very skilled at smoking weed.