Why Flashing Fails Before the Shingles Do
Asphalt shingles and metal flashing are both built to last for decades. The weak point is what joins them: sealant, and on pipe boots, rubber or neoprene. Rubber degrades under UV exposure and Naperville's freeze-thaw cycles faster than the asphalt or metal around it, cracking and losing flexibility well before the shingle field shows real wear. The same is true of the sealant beads at step and valley flashing seams — they harden and crack years ahead of the metal or shingles they're sealing.
That's why a roof can be structurally sound while still leaking: the flashing components are simply the first thing to age out. It's also why flashing repair is often the right, proportionate fix rather than a sign the whole roof needs attention — see our repair vs. replace guide for how to weigh isolated flashing work against full replacement.