This homeowner in Billerica, MA contacted Mighty Dog Roofing after experiencing an active leak at the area where the roofline meets the siding — one of the most common and often overlooked failure points on Massachusetts homes. Years of freeze-thaw cycling, wind-driven rain, and seasonal expansion had compromised the existing flashing system, allowing water to penetrate at the transition walls. We completed a full flashing repair and re-flashing of the entire siding-to-roofline transition on both sides of the affected section, addressing the root cause of the leak rather than applying a temporary surface fix. In addition, the EPDM rubber section at the corner where the rubber membrane meets the roofline was restored to full watertight integrity — a critical detail that is frequently missed in standard repair work. To reinforce the pipe boot area and eliminate a secondary water entry point, Ice and Water Shield was applied around the boot to create a fully sealed, watertight barrier underneath both the boot and surrounding shingles. Any deteriorated or rotten wood decking discovered during the process is addressed with matching CDX plywood or ledger board replacement to ensure a solid substrate before new materials are installed. All waste materials were removed and disposed of as part of the scope, and any additional work identified on site is communicated directly to the homeowner through a formal change order process — nothing is done without explicit approval. This type of targeted flashing repair is particularly important in Massachusetts, where ice dam formation and heavy seasonal precipitation consistently stress transition zones between roofing and vertical wall surfaces. If you're a homeowner in Billerica or the north of Boston area dealing with an active roof leak or failing flashing system, schedule your free inspection today.