Can a handyman fix a roof leak?
A handyman with caulk might hold a leak back for a season or two. A repair that lasts is roofing work.
Most of the job is finding the leak. A ceiling stain shows where the water came out, not where it got in, and the real entry point is often a flashing detail several feet further up the slope.
Know what you are paying for. Caulk smeared over a joint is upkeep. New step flashing, counter flashing cut into the mortar, a new vent boot or a relaid valley is a repair. Ask which one is in the quote.
Anyone working at height on your roof should carry workers’ comp and liability insurance. Ask to see proof before they climb.
If a caulk patch has already failed once, book a leak visit and we will find and photograph the detail that is really letting water in.