When masking for trim, there is a window of time where you dont want to pull tape, as the trim enamel is very rubbery, but hasnt 'bit' into the surface yet, so its prone to pull off with the tape. My rule is, either pull it while its wet, which only works if you're doing something small, or wait a day so the paint can cure and stick to the trim better, and have less chance of pulling up in a rubber sheet.