This happens quite frequently when people are going to make a big purchase or pay off another loan with worse terms. It's not as much of a red flag as you would think.
Problem is, the police seems to be spending the resources that should be monitoring those people on monitoring everybody.
The other thing to consider is what flags actually allow the authorities to do unless the flags rise to the level where the police can actually arrest the suspects or follow them around 24/7.
The point is that we should really consider the wisdom of a surveillance state that we're increasingly tolerating in the US. It is not illegal to be an extremist until you've broken laws. It is illegal for the government to deprive people of their constitutionally guaranteed rights. Like it or not, the rights that we enjoy have to apply to everyone or they aren't worth anything.
No it isn't because no agency has enough manpower or resources to follow up on every lead a 'terrorist detection model' generates. Catching bad guys isn't all tech. At some point, a human being has to get involved to investigate if they're actually planning to commit an attack.
Of course there's a purpose in having a government that looks for terrorists - but it is too easy to turn those capabilities into suppression of dissent. Did you see how in Paris they used their new emergency powers to PREEMPTIVELY put people who had protested against climate change in house arrest. Before they even had their convention. That was horrible.
The same exact thing happened in the Paris attacks: one of the killers (already known by french authorities to be radicalized) withdrew three months of salary shortly before the assault.
Saying that encryption is the problem is simply ridiculous considering the fact that even the most basic procedures aren't being taken care of.
Having access to encrypted communications is just going add a lot more information to monitor and thus more noise to filter out for federal agencies, who are already bad at catching the red flags.
The answer here isn't MORE surveillance, it's more TARGETED surveillance ie devising much more precise warning patterns to look out for. For example, the San Bernardino killers apparently took out a massive loan and emptied their bank accounts prior the attack.