Hot take: a broken HubSpot sync ate 11 days of my quarter, and the fix was one checkbox
A contact property got mapped to the wrong object during a Salesforce integration in March, so every quote revision duplicated the deal and our pipeline report was off by 30 percent. It took 11 days of digging through sync logs to find out someone had left 'create new records' enabled, and unchecking it fixed everything in 2 minutes. What's the dumbest one checkbox mistake that has cost you a sprint?