Dumb question.. roof leak

[Moth]

Is the leak in the area of a plumbing vent through the roof?
The "boots" around the vent pipes often go bad, and a crack can open up and let water in.

That was going to be my suggestion. The plumbing vent on my roof was letting in water so I caulked and replaced the flash.

[chet everett]

Mike:

Those are some of the best/worst photos I've ever seen. I bet you have some stories to go with 'em! It is amazing/annoying how damaging water can be. In my mother's house the gable end vent would admit SNOW that was blowing from just the right direction. The stuff would pile up against a joist and them as heat from the house would melt the water s-l-o-w-l-y drip in. Easy to fix by putting some additional baffles behind the gable end vent, but VERY tricky to track down unless it was actually happening...

[Keeper]

I had a similar issue even after having a new roof put on. It was the flashing around the chimney. Turns out the way the roof was built allowed leaves and other stuff to get under the flashing during a hard rain. The guy who put on the new roof came back out and fixed the flashing so it wouldn't lift up. That fixed the problem
When I had the old roof removed, he discovered there were termites around the chimney which weren't discovered during the home inspection only months before, due to the way the addition was built, they couldn't get under it to check for termites.

[marlon hernandez]

If you have more then 1 roof the water will travel between the two roofs to the path of least resistance always good idea to remove all roofs before reinstalling