That's bad DMing or a player attempting something impossible. If it's the latter I'd just tell them it's impossible. But if it was a skill challenge it wouldn't automatically change anything, after all you can't repeat skills without penalty. Make the skill challenge tough enough and those 3 failures will accumulate anyway. If you feel what is happening isn't fun or fair you need to talk to the DM. Changing how the DM is setting the PC up for failure doesn't change anything.What that means is, every infiltration attempt will fail. Because the DM will simply keep throwing checks until one fails, and then the whole thing falls apart because every fail is a catastrophic failure. There are no degrees of failure. Did you fail your deception check? Yes, then the other person automatically sees through your disguise and raises the alarm.
Every.... single... time.
Oh, and just like 4E, 5E talks about success at a cost when the PC fails.