Plumbing free standing wood stove into a 6”x8” clay chimney flue

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Update:

Broke all the clay, what a mess that was. Sent the liner down the chimney this morning and got snagged about 18’ down. I twisted, wiggled, spun, anything I could do to get past that point, but couldn’t. This point in the chimney doesn’t look quite plumb and there’s a little mortar from a joint. Ordered a pulling cone. Going to give it another go when the cone arrives.
 
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Update:

Broke all the clay, what a mess that was. Sent the liner down the chimney this morning and got snagged about 18’ down. I twisted, wiggled, spun, anything I could do to get past that point, but couldn’t. This point in the chimney doesn’t look quite plumb and there’s a little mortar from a joint. Ordered a pulling cone. Going to give it another go when the cone arrives.
I had one offset in a 12x12 with some mortar sticking out. We had two people up top and one in the basement and just barely made. I used abs shoving that liner down I didn’t know I had.

Remember you can pull flexible liner apart. If you can see the mortar maybe you could get creative and remove some of it.
 
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It might be good to lower a camera down there. Maybe use a cellphone securely strapped to a rope?
 
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I had one offset in a 12x12 with some mortar sticking out. We had two people up top and one in the basement and just barely made. I used abs shoving that liner down I didn’t know I had.

Remember you can pull flexible liner apart. If you can see the mortar maybe you could get creative and remove some of it.
I’m thinking about sending the tile breaker back down and chipping it a little bit. I can see it from the top of the chimney.
 
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U might be able to knock the mortar squeeze out off with 2 10ft 3/4 or 1" pvc pipes screwed or glued together. That's what i use as my chimney brush extensions. I tape the brush connected to 1 length of chimney brush rod to the pvc. Then when i get 10' down i can put the 2nd 10 ft. male end in the female end and i bolt them together thru a hole i drilled in each one. Works great.
 
I’m thinking about sending the tile breaker back down and chipping it a little bit. I can see it from the top of the chimney.
That sounds like a good plan.