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This is always tricky. If your starting a new project and have the choice, then put the stove pipe at the peak of the roof. This way you can simply cut a hole in the metal/sheathing and put the stove jack (flashing) on top of the metal roofing with the ridge cap covering the top lip of it. If you must install midway or at the eave of the roof, then extra special care must be taken to prevent leaks. Think about the fact that the water must always be directed down hill, and care must be taken to keep the water from siphoning back up. I use high quality caulk like Proseal or Lexel to make a gasket between metal to metal connections. There are also high temp rubber boots that can make this job easier. More expensive but fast to install. Follow the manufacturers directions and if in doubt, have a professional do the job. I have seen so many homeowner installed chimneys/flashing fail over the years. It results in costly water damage, stove pipe damage and at least a temporary loss of service with the stove. Good luck. I did several of these before I got good at them. Invest in several pairs of tin snips to make the cuts required to do the job.

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