Repairs & leaks
Roof Repair and Leak Tracing
Nine times out of ten the leak is not above the stain, and it is flashing rather than shingles. Finding it costs less than replacing what was fine.

Water gets in somewhere high and shows up somewhere low. Sometimes several metres away, having run quietly along a rafter the whole distance.
So the stain on your ceiling is where the water finally gave up. It is not where it got in, and quoting a repair from the stain is guessing with a ladder.
It is usually the flashing
The open field of shingles — the big plain area everyone pictures when they think "roof" — is generally the part still doing its job perfectly well. The failures happen at the interruptions.
A chimney. A valley where two planes meet. A skylight. The step flashing tucked behind a dormer or a rear addition. And the plumbing stack boot, which deserves its own paragraph.
The stack boot, which is the answer more often than you would think
It is a rubber collar around a plumbing vent pipe, sitting in full sun for two decades. Eventually it splits. Water runs down the outside of the pipe, into the attic, and the stain turns up a metre away looking like something far more serious.
Cheap part. Short job. A genuinely large share of the calls in this trade, and one of the more satisfying phone calls to make — no, you do not need a roof, you need a forty-dollar boot and an hour of somebody's time.
Repair, or replace
A roof with ten good years in it and one failed boot needs a boot. Easy.
A roof at twenty-two years, with shingles curling at the edges, granules collecting in the eavestrough and a third leak since spring, is being repaired past the point where repairing is the cheaper option. That is a harder conversation and we would rather have it honestly than sell you a fourth repair.
What decides it is the deck and the age, not the leak. Either way you get the findings in writing — including when the finding is that the roof is fine and your water is coming from somewhere else entirely, which happens more often than you would expect.
Talk to a Woodstock roofing contractor
Three things get us most of the way there: which town you are in, roughly when the roof was last done, and what you are actually seeing — a stain on a ceiling, granules in the eavestrough, shingles on the lawn on Sunday morning. That is usually enough to tell you whether this is a repair, a claim, or a roof that has quietly reached the end, without anybody driving anywhere.