Repeated leaks
If water keeps entering in different areas, the roof may be failing as a system instead of in one small spot.
Worn shingles
Brittle, curling, cracked, or missing shingles can make it harder for the roof to shed water reliably.
Soft or damaged decking
Soft areas, sagging, or visible damage below the shingles can point to problems a simple surface repair will not solve.
Need someone to look at it?
Send the town, what you noticed, and any safe photos. A clear first message helps the team understand whether you need a quick check, a repair, or a larger project quote.