Yes you need to extend it and brace it. I put braces on chimneys all the time do it right and it won't leakSeriously, if we have to make the chimney taller, HOW? When we put the addition onto the house, we can actually make it a lower room (think bi-level). The land is sloped down immediately in front of the house so it'll actually be easier to build it a few steps down. That will make it easier to have a higher ceiling in that room--perhaps 4-5 feet taller. What I'm getting at is that if we were to move the wood stove to the addition, the chimney wouldn't have to stick up quite so far above the roof. My husband's concern is that if we make the chimney taller, we'll have to brace it, which means risking more roof leaks where the braces are attached to the roof. Every place he has to drill a hole or drill anything into the roof, there is the potential for leaks. Any other suggestions?