So we have two options:
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A 52 year old federal judge is somehow tech illiterate in a way that would imply they have absolutely no idea about the fundamentals of modern technology.
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A federal judge is asking a large number of extremely basic questions to get their answers on official records so that the cases parameters are clearly defined. He is taking extra care because there's not a lot of direct precedent on these issues.
I'm heavily leaning towards number 2 here. The internet likes to pretend everyone over the age of 40 has no idea how a computer works. The year is 2023. A middle-aged person today was fairly young when computers started to be incorporated into all aspects of society and is well versed in computer literacy. In some ways they are actually much more tech literate than the younger generations. It's almost certain that he knows the difference between Firefox and Google.