Where masonry and roofing meet
Most of what gets reported as a roof leak in Connecticut enters at a junction, a chimney, a wall, a dormer cheek, a skylight curb, a valley. That junction is precisely where the two trades meet, and it is where responsibility gets passed back and forth: the roofer says the chimney is failing, the mason says the flashing is wrong. Frequently both are true, and the homeowner pays for two visits that fix nothing.
The same thing happens on the ground. A blocked gutter or a downspout discharging at the wall is a roofing detail that produces a masonry problem, saturated backfill, frost pressure and water pushing through a foundation joint. An ice dam is a roof symptom of an attic problem. Treating these as separate trades is why the same defect gets paid for repeatedly.
That is the reason this directory covers both. When you request quotes, describe the whole symptom, where the water shows up, when it happens, and what the weather was doing, rather than naming the trade you think you need.