Water is amazing in its ability to find the path of least resistance. Sometimes it's extremely obvious, sometimes not. It is hard to see on a phone, but that flashing detail is kind of odd. I have to wonder if the shingles are properly overlapping the flashing and that there aren't spots where it is trapping the water, instead of shedding it. I would doubt it is related to the brick or the mortar, but if there is a path, water will find it.