Yeah, it's never on purpose. Nobody's ever that Machiavellian (at least not successfully), mostly because there's genuinely never a need to do silly things like that unless you're a legit "can neither confirm nor deny"-tier spy.
Ross Ulbricht remains my favorite example of how complacency can undo even very good opsec. He wasn't particularly arrogant, didn't taunt the authorities about failing to catch him and only came to their attention in the first place as a fluke when an investigator came across a decade-old forum post he made about, well, building a darknet supermarket for naughty things. Even then, it was only enough to identify him, not charge or convict him.
They finally got him at a public library using a public computer (running Tails via USB flash drive, practicing the usual opsec). They arranged for a pair of attractive women to create a distraction nearby (a catfight), and in a moment of absent-mindedness he stepped away from the console to investigate ... and left it unlocked. The feds grabbed that computer before he could get back to it, and since it was signed into enough of his "empire" to help the feds put him away forever, that was the end of it. Caught him red-handed by baiting him into thinking with his dick.
A single mistake and a moment of weakness was all it took, and he practiced good opsec. These trannies? lolno. Nobody who can convince themselves that they're somehow the opposite sex despite all evidence to the contrary is capable of forming the same internal logical consistency and discipline needed to maintain good opsec. Add hubris and arrogance to it and these troons might as well just start posting their dox directly themselves to save time and embarrassment.