Water tends to travels before it drips down visibly. Interestingly, a leak can come out twenty feet away from the original leak in a roof.
The most common weak spots on your roof are areas that need protection from flashing. However, damaged shingles or damage in the waterproofing material which lays underneath the shingles are also common causes of roof leaks. A leak may not mean you need to replace your entire roof. However, if the leak has persisted lasting long enough without management, there is likely dry rot involved – or the roof is very old – it may be time to get it replaced.
These pipe jacks have a rubber boot that will only last 10 - 12 years (not as long as your shingle), and should be inspected and completely replaced as necessary. When they leak around the boot or even are lifted by the wind, they cause severe damage to the decking and obviously to the interior of your home.