Hip Roof Chimney Flashing question

I recently bought a 90 year old house that had roof leaks around the chimney, and evidence of many years of water issues in the area. I already had the chimney replaced above the roofline, a new chimney flashing, and new roofing put on. The leak persists despite several attempts by the contractors to fix it. The chimney/flashing guy will be back again next week to give it a 4th try.

The main problem is the location of the chimney. One corner of the chimney is right up against one hip of the roof . . . snug against the hip rafter. The flashing can’t go up much and the cap shingles can’t go down much. The previous owner “solved” the problem by encasing the entire area under about an inch of tar.

Is there a really slick and professional way to deal with this problem . . . some clever flashing configuration that doesn’t involve gobs of sealant? Help please!

Posting pics is always helpful to us when trying to make a diagnosis. There is no reason for “sealant” around a chimney flashing. Someone with skill can design a working system that is nothing but copper, solder and mortar. If your chimney is stucco, stow, siding, etc the obviously it should be under that material. The only place you might find urethane is if you cut the counter flashing into existing stucco let’s say.

Posting pics would help us give more detailed info. Your problem may also be the chimney or chimney cap and not the flashing. You can always wrap the chimney in plastic and if it still leaks you know it is leaking at the base (flashing). If it no longer leaks then your problems lie above the roof line and you need to call the mason…

Yes. It’s easy for any Roofer to fix. No gobs of glue needed either. Nothing special needed either.

ok you said shingles and an inch of tar in the same sentence.
thats not good.
best thing to do is water test the roof for awhile
and then move up to the chimney.
find were the leak is coming from.