They hadn't integrated AI into their decision tree in order to strike. This is entirely the fault of humans. AI don't give assessments in that field. AI may give identification on these assets, (It's 3x adult males) but the person monitoring that AI is the one who makes assessments. I know this was planned but it wasn't integrated when I was in the know.

All a LLM would be able to do is identify what type of boat there is and a guess on how many people there were. Not who those people are. At least not for people who are unimportant as these people were to grand scheme of operations. It may be able to identify a high value individual (HVI) but that sort of person would never be a drug runner

The assessor would keep a more reliable tally of people. People much higher up the chain would be the ones to actually call for the strike though.

The US military was trying to integrate AI into their workflow but in ways that actually make sense. The people who are actually responsible for the integration of things into combat systems are really freaking smart. (It's not the same as that 36-year-old Master Sergeant who thinks that the best part about AI is making music that doesn't know the meaning of structure) The military also has an institutional conservatism where they don't want to make changes that are really stupid so they have to plan out everything. That's one of the many reasons why it costs so much to procure anything.