In general, PbtA games aren't really "I do it again" kinds of games, so using the same move over and over isn't really the intent. For instance, take the basic move "Investigate a Mystery" as an example: the explicit trigger is "when you investigate a mystery..." You make your roll and get clues, and that mechanism represent you examining the clues before you to the best of your ability. But that's it, you've investigated the mystery. You've exhausted all of the leads and followed every available line of inquiry. You don't get to just roll again because the conditions that trigger the move aren't met. You'll note that there's no move for "when you reinvestigate a mystery..." You've learned everything you're going to learn - until you're presented with a new mystery, that is!
This is how the Keeper controls the pace of the story, how the underlying mystery gets revealed little by little as the PCs get more information. Otherwise, if you could just keep rolling and re-rolling the move, you'd quickly exhaust all of the clue options and know exactly what you're dealing with. But that's not how MotW works, because it's driven by the narrative rather than the dice.
This will feel weird to people used to traditional RPGs where you keep making "search" rolls until you find the secret door. PbtA games are explicitly not that. So yeah, take a good hard look at the trigger for "Oops!" and make absolutely sure it's applicable before having the player roll anything.