Leak around Chimney Flashing - some beginners Questions

Hi Everyone,

I’m reaching out because I am in a pinch. We removed the old fireplace a couple of weeks ago with the plan to add an insert. Lucky us that we didn’t have time to add the insert faster because we had some strong rain falls a couple of days ago, and we noticed some water dripping down, inside the chase on the high side of the roof. The low side and sides were dry. The wood where the drips came down still looked fine so it must have just started. Anyways, I went up on the roof (we bought the house not too long ago) and while the asphalt shingles looked in decent shape, the flashing looks poorly done and water/snow can collect between roof and chimney.

The issue we have is that we live in a remote northern Canadian town, winter is coming fast, and the two roofers in town are too busy to help out. So I took next week off and I guess it will be me doing my best to fix it. I have only ever installed a shed roof.

My guess is that the leak is somewhere around the flashing, but I guess I will know for sure once I remove some of the shingles and the old flashing. My plan is to remove some shingles around the chimney, add another layer of roofing felt and redo the flashing and add shingles. I have a few questions that I hope you can answer:

  • is that even the right approach?
  • if the leak is close to the flashing, how much of the old shingles around the chimney would you remove?
  • is it advisable to add a saddle or cricket?
  • if the leak starts higher up, is it enough to trace where it starts then add roofing felt and replace shingles from there on or would it be better to redo the entire side of the roof the chimney is on?

I would really appreciate any help!


Get some decent pics of the chimney, cap, and flashings.

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Remove shingles and underlayment until you find water stains, shouldn’t be very much if it’s flashing related. Use ice/water shield on the redo.

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