Why My Roof Leaks Around Pipes?

When a roof starts leaking around a pipe, homeowners often assume the shingles have failed. In reality, it’s usually not the shingles — it’s the penetration.

Plumbing pipes, mainly waste stacks, extend through your roof and must be properly sealed. The flashing that protects these pipes is called a roof boot. Its job is to create a watertight seal where the pipe meets the shingles.

Over time, boots can crack, deteriorate, or loosen. In Chicago, we commonly see lead boots damaged by squirrels chewing on the soft metal. Once the boot is compromised, water can easily enter around the pipe and cause interior leaks.

At Anchor Point Roofing, we take pride in completing roof repairs the right way — not just patching the surface. When repairing a leaking waste stack, we remove the damaged boot, install new synthetic felt around the penetration, properly secure a new boot, and install a new shingle that matches the existing roof as closely as possible.

If you’re experiencing a roof leak around a pipe in Chicago, addressing it early can prevent larger water damage.

You can also watch our YouTube video explaining this repair in more detail here:

👉 https://youtu.be/LK3epwwsTAQ?si=pd7K2oQjdOPa6B1x

Location: Chicago, IL