Do you let a player reroll an ability check after they have failed? Depends. If there's no consequence for failure and time isn't a factor, why even have them roll in the first place?

— Dan Dillon (@Dan_Dillon_1) January 3, 2021

Sometimes.
But a game with no chance of loss isn't a game anymore, it's low impact improv pic.twitter.com/SQ3cEkCRD5

— B. Dave Walters: Revolutionary Content Creator (@BDaveWalters) January 3, 2021