Remember that stealth is NOT INVISIBILITY.
Where stealth gets vague is when players ask to stealth in a logically impossible place (open flat ground, through a watched door, across an open bridge, through a straight flat stone hallway).
There's generally a few options to go with: 1) let the dice roll and as a DM somehow explain the high roll. 2) explain the situation and tell them it's impossible, unless they can explain how they can possibly sneak in the situation. Either the player will convince themselves out of the action, or they will convince you of their approach. 3) Allow them to attempt option but with high DCs. If you go with this approach, it should actually be possible to roll high enough. Otherwise you are going to cause arguments OR at best wasting your time and your players to resolve an impossible action. Remember when a player rolls, they will believe that it's a possible, telling that they failed on a Nat 20 only makes them feel like you are cheating or wasting their time.
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