Leaky Roof & Gutter Survival Guide: How to Find, Fix, and Prevent Costly Water Damage

6. Leaks at Walls and Dormers

Not all “roof” leaks start on shingles. Wind-driven rain often sneaks in:

  • Around windows in dormers
  • Between corner boards and siding
  • Through cracks, gaps and knotholes above flashing

Water can bypass step flashing, run behind siding and show up as a roof leak.

What to check:

  • Old, cracked or missing caulk between corner boards and siding
  • Gaps around window trim
  • Damaged siding directly above step flashing

Fixes:

  • Dig out suspect caulk with a putty knife and replace with high-quality exterior caulk.
  • Replace any rotten, cracked or missing siding, overlapping step flashing by at least 2 in.
  • If leaks persist, remove corner boards and inspect overlapping flashing in the inside corner — often you’ll find old hardened caulk blocking proper overlap.

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