How to stop this small roof from leaking

A few additions to Jeff's advice if you decide to replace the damaged drywall.

1. I'd suggest you look into waterproof drywall or mold resistant drywall. There are various products that do a better job than the typical green board that you would use in the bathroom that will help if you are installing in an area that has a lot of exposure to the elements.

2. Double check the thickness of your drywall if you are patching. If you replace a 5/8" with 1/2", you'll notice it.

3. Use screws, especially on the ceiling. They take more time, but hold better and are less likely to cause the nail pops that you are seeing.

That being said, I think it's entirely possible that you're just more aware of drywall issues and there may not be anything wrong. To know for sure, I'd go up to the attic, pull up the insulation where you suspect damage, and look for water rings or other mold growth. Use a flashlight, no need to feel with your hands (and risk falling through). While you're there, check the insulation for blackening that would indicate mold is growing there, and if so, replace any damaged pieces.

Your ability to see the joints between the drywall is just a sign of not enough paint and/or primer. And popped nail heads are normal as a home moves. My personal plan is to replace all the popped nails with screws and double up on the spacing the next time I paint to minimize this issue.

Options include looking for discoloration on surrounding areas and even putting a paper towel or Kleenex in suspect areas in order to detect a small leak that may not have been sufficient to create noticeable discoloration. Depending on the volume, you may be able to hear dripping in order to help trace the leak. And you may wish to reconsider whether the initial diagnosis was correct or whether the repair was sufficient.

Here are three causes that weren't obvious to us that you may wish to consider:

(1) Around the tub spigot: We had a situation in which we had a leak from a bathroom on the ceiling of the dining room beneath it. We re-caulked the tub and shower surround, did a small test, didn't see any water leaking, and thought we'd taken care of the problem. The next time someone showered the leak reappeared. We eventually figured out that the problem was around the spigot: Water from the shower was hitting the spigot, and because there was not a good seal around the spigot, water was running behind the spigot, down to the floor, and eventually into the dining room below.

(2) The actual copper supply line connections--if you're fortunate enough to have access to them without tearing out the wall: In another house, one with only one floor, we thought we had a leak in our shower pan, but during a remodeling discovered that the hot supply line had not been soldered correctly and water had been squirting out between the wall and eventually out through the brick in the adjoining exterior wall.

(3) Diversion due to insulation: We had another leak that we thought was due to a problem with the flashing between the roof and adjoining siding. After tearing up the roof and the ceiling of the room being damaged, we discovered that the problem a poorly-sealed nail in the roof itself. However, this location was several feet away from where water damage showed up. In this case, the insulation directly below the small leak was sufficient to keep the water from running straight down. Instead it wound around and into another room.