I have frequent crazy emails getting past gmail spam detection (I've reported and even reached out to support who does nothing. Well they blamed Microsoft...).

The email appears like normal spam just like this one. Things that a Naive Bayes filter should catch... But if you open up the original message there is about 20 pages of text there and they are filled with stuff that looks like password reset emails, account creations (ironically one has a email link for OpenAI account creation), universities, and so on. Recent emails are getting a lot smaller (maybe a few pages) but clearly what's going on is that they were just throwing shit at the wall and seeing what stuck. I've saved a bunch of these because they are actually quite fascinating. Not sure if anyone does research in this but I'd share for that (don't want to dox myself to all of HN though)