I've found that when the players hit an outright failure, a lot of the time they just draw blanks or zero in on this one specific solution. It's a weird tunnel vision.
Like, they want to talk past the doorman and he says no after they roll. Good players on their game will then think about other options. Sneak in the back. Set off an alarm. Impersonate someone who lives there. But i've just had so many players that just get stuck on this, and will try to spend 10 minutes on "What if I ask him nicely?"
I've started including a spiel about this in my session 0. "If an obstacle in the world has exactly one purpose in the story, and you attack it dead on, you may fail. Especially if it's not also your strong suit. For example, there is a doorman of a fancy apartment building. His entire role in life is to look at people, and only let them in if they're authorized. If you walk up to him, not authorized, and go 'Hey bro let me in', that will be a very hard check. That is shooting fire at the fire elemental. Disguising yourself will be easier, but still is in his domain of 'Looking at people and only letting authorized folks in'. But going in a back door so he doesn't see, setting off the fire alarm so he evacuates, calling on the phone and telling him his car has been towed, those ideas hit him where he's weaker."