We have one of those old ugly popcorn ceilings in one of the dens. The roof had a small nail hole where water leaked in and discolored the popcorn ceiling. I fixed the roof, but the ceiling is still discolored no matter how many times I paint over the thing. I think this summer is the one where I'll be putting in a new flat ceiling in that room. I stopped using the room because all I saw was that stained ceiling.
Those old popcorn ceilings can be a pain sometimes and are hard to repair and paint. Have you tried some of the spray Kilz to cover the stain first then try to paint it?
We have popcorn ceilings too and I hate it. I would take the popcorn down but it's a big pain so it's just easier to leave it up for now.
We have tried everything, including primer and Kilz. Nothing short of replacing the ceiling is going to work. I just dread all that plaster dust that pervades everything all through the house, no matter how much we cover things up.
Fryar we have the exact same problem, unfortunately we have that ceiling in the entire house. The roof leaked and stained the popcorn ceiling in about 3 places. It really sucks. I wouldn't mind getting rid of it entirely though. Let us know how it goes.
Wet the popcorn with either a spray bottle with warm water or a wall paper steamer and scrap that crap off. Skim coat with joint compound, sand lightly and repaint. OR......lay 3/8" sheetrock over it, tape and paint. OR....rip it all down and start over.