While this isn't what I wanted to hear, I appreciate the quick reply. I went downstairs and examined the coupler.... again. I think the sleeve was hung up on a piece of garbage stuck to the side, but I can't really be sure. When I removed the sleeve, the rubber seems perfectly aligned on both the CI and PVC sides. both of the cuts were very straight, so they fill the rubber gasket all the way to the center on both sides. I also wire brushed that heck out of the CI section to be sure and remove all of the gunk that was stuck to the sides (I do notice a slightly raised seam on the bottom from casting though). I wonder if this piece of CI has a slight flare to it? Not sure, but it looks a little flatter now when tightened. Again, I ran a ton of water through this after reassembling and there is absolutely no leaking whatsoever. I also took a look at several pieces of CI that I have laying around from this project (removed from the ground) and everything that I see has a larger outside diameter than the PVC pipe. I'm not sure what else I can do here.