Have you ever noticed a stain in your ceiling and thought that you probably had a bad roof. The most common roof leak occurs around plastic plumbing pipes and fortunately it is one of the easiest repairs to detect and correct.
If attic access is simple enough you may feel around these plastic pipes for wetness (during a rain) or look at where the pipe exits the roof for daylight penetration. Cracks in the rubber seal around the pipe will allow water infiltration. A simple on top of the roof inspection will reveal whether or not the pipes are in need of repair. Around these pipes there is a hard piece of plastic which sits on the roof and a rubber ring integrated into the top of it which surrounds the pipe making a watertight fit. This entire component is often called a roof jack. The rubber portion of this roof jack will often begin to show visual signs of deterioration seven years or so after the roof has been installed. This will allow water to penetrate this seal causing a leak into the attic and possibly onto the ceiling below.
It is common for roofers to replace the roof jack however; a new rubber gasket is almost always all that is needed. Unless the hard plastic portion has been cracked or damaged in some way it does not need to be replaced. On rare occasions when they do need replacement, the shingles will need to be separated from around the pipe area. Sometimes the shingles are sealed so tightly that is almost impossible to separate them without damaging them. A new pipe gasket is a perfect and inexpensive fix. It is much better than using asphalt roof cement which will crack when the sun dries it out causing another water leak to occur.
A homeowner who can safely access his roof could easily perform this repair himself. If safe roof access is questionable, someone cleaning your gutters or painting your home may be an inexpensive alternative. This rubber gasket simply slides down over the pipe snugly. A roofer would normally charge from $175.00 to $300.00 depending on the level of difficulty involved to replace the pipe jacks on your roof. The cost of the new ring is around $4-$8 at most home improvement stores.
A relatively quick and easy repair that could save you hundreds of dollars in damage to your ceiling below!
Beginning stages of deterioration
A very badly damaged boot
Adams Home Inspection Blog 
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