There are several items on any given roof. One of the smallest items are pipe boots or pipe collars. These are the black rubber and PVC units you see on the bottom of those white (vent)pipes protruding from your roof. Their purpose is to prevent water from penetrating through the hole in the roof deck.
As you can see here, this boot is severely cracked. As a result, every time there is rain, the attic below is getting wet. Left unchecked, penetrating rain water will begin to rot the plywood or OSB (Orient Strand Board)decking creating a more serious leak issue.
Generally the pipe boots will start to deteriorate in 7-10 years after they are installed. Certainly their exposure to the sun will increase the deterioration process. The seal on top becomes brittle and begins to crack.
In a sense, pipe boot failure is much like brake failure on your car. Rarely, do the brakes go bad on both wheels simultaneously. The same is true with pipe boots. Not every boot on your roof will fail at the same time. But with some time, all the other boots will begin to fail as well.
However, just like brakes, your mechanic will recommend replacing both or all brakes simultaneously. It is wise to replace all pipe boots at once. By doing so, you will have the satisfaction knowing your roof will be "water-tight" at those vent pipe (boot) penetrations.
If you have a pair of binoculars, why not have a look at the pipe boots on your roof? If you do not see any indication of cracking you can be sure they are doing their job. If there is evidence you should contact you roof contractor to have the boots removed and replaced.
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