Debris like leaves pine needles or twigs can trap water against the roof.
Leak along outside edge of roof.
Make sure you keep the roof clear so water will spill over it fast.
It should overlap another piece of ice and water barrier laid below all the way down to the roof edge.
This means the expanse of shingles slate shakes whatever.
Dormer leaks can be caused from a number of issues.
Then reshingle sliding metal step flashing behind the fascia board the trim behind the gutter.
And in our experience when a single piece of flashing extends only a few inches under the shingles especially on a long roof slope and worse on a roof that happens to slope slightly towards rather than away from the abutting vertical building wall the accumulated roof drainage water near the bottom end of the roof wall intersection will overwhelm the width of the flashing and because it is not directed back out on top of successive shingle courses it leaks into the building or building.
Rotten or missing trim or siding can allow water to leak behind flashing and into your roof.
Look for cracks in the base of flexible rubber flashing or broken seams in metal varieties of vent pipe flashing.
This should cover the most leak prone areas.
If your roof is asphalt then you can walk around with ease.
Worn out flashing or missing sealant can also cause roof leaks around dormers.
The water can seep into the roof.
The rubber gasket that surrounds the vent pipe could be rotted.
A roof leak at the edge of a dormer can allow a lot of water to enter your home.
Depending on how the roofs join you may have to cut a slot to work it in far enough.
If your roof is older it is possible that the leak is within the roof field.