Why Is My Roof Leaking Around a Penetration and What Should I Do About It?

A roof leak around a penetration—such as a pipe, vent, or chimney—is often caused by improper or aging flashing. Flashing is the metal or membrane system designed to seal these vulnerable areas, and when it is missing, damaged, or not installed correctly, water can easily find its way into the roof structure. Over time, sealants can also dry out or crack, making the problem worse and leading to interior leaks, stains, or even wood damage.

In many cases, the issue is not just surface-level—it may involve deteriorated underlayment or previous repairs that were not properly integrated into the roofing system. That’s why a thorough inspection is essential to identify the true source of the leak.

For roof leak repair in Chicago, Anchor Point Roofing provides a detailed and reliable repair process. Our team carefully inspects the base of the roof penetration to determine the exact cause of the leak. We then remove any compromised materials and install new synthetic felt and ice and water shield as needed to strengthen the protection beneath the shingles.

Next, we install new shingles that closely match the existing roof to maintain a clean and consistent appearance. Finally, the roof penetration is sealed using a commercial-grade roofing sealant to ensure a durable, watertight finish that can withstand harsh weather conditions.

With the right repair approach, roof penetrations can be properly sealed and protected, helping prevent future leaks and extending the life of your roofing system.

Service provided: Roof Repair

Location: Chicago, IL