Yep, definitely poor workmanship, I will need to address that. However, I dont think that is the reason for the water leaking onto the brick. It looks like its because the gutter is about half an inch away from the brick and there is no sealant.
I agree with you that whatever is going on with the step flashing, or lack of it, may not be what’s causing your problem. You do have to wonder why whatever that is where the wall meets the roof (still looks too thick to be caulk or sealant looking at the pics on my phone. I’m guessing foam) was put in there. It’s really inconceivable that anyone would not install some type of flashing there. I was just discussing fixes for missing or worn out step flashing on something where you can’t get behind the siding.
Can you get up there and get a picture? It would sure help. Get a picture of whatever that is put on there, and one where the kick out flashing comes to the gutter. We’re just making guesses looking at pictures from the ground. You might even be able to see the flashing. The shingles are not supposed to be pushed right against the edge of the flashing where it 90’s to the roof. They’re supposed to be left shy just 1/4 to 3/8 so the water can move down easily.
I don’t agree that the problem is the gutter not being sealed to the brick. That is not standard or something that is normally needed. In fact, jamming the end of the gutter into the siding, then sealing it, would be a no-no. If that was wood siding, would you want a metal gutter jammed up against it trapping moisture against the wood? No, it would cause rot.
The correct way is step flashing overlapping a kick out that directs the water into the gutter. The back side of the kick out should be sealed, but that doesn’t seem to be your problem.
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