I painted my living room last month and thought I'd be smart and caulk the baseboards after painting. Big mistake. The caulk wouldn't stick to the fresh paint and I ended up with a smeary mess. Had to scrape it all off and start over. Next time I'm doing the caulk first, then painting over it like a normal person. Anyone else learn this the hard way or am I just slow?
Three months ago I did nearly the exact same thing in my hallway and spent a whole Saturday fixing it. The paint had only been dry for about two days so the caulk just slid right off like it was greased. What really drove me crazy was having to buy mineral spirits to clean it all off that fresh white paint without ruining it. I figure the paint needs at least a full week to fully cure before you can even think about putting caulk on top. Now I just do the caulk first like you said and paint over it with a small brush and it takes half the time. Is there any reason people don't teach this stuff in school or what.
Mineral spirits on fresh paint is a nightmare, I feel your pain on that one. You're dead right about the cure time too, that paint needs to be fully hard or the caulk just peels off like you described. I've started using a damp finger to tool the caulk joint, and if I see it pulling away from the paint, I know I messed up. The whole paint-then-caulk thing is a trap because nobody tells you the paint has to be rock solid first. Caulk first, paint over it, that's the only way that doesn't turn into a Saturday project.