Sorry I wasn't specific enough, ImageOptim uses PNGCrush and a bunch of others, it's just a GUI front end to them all. The issue I was having was with JPGs and not PNGs, not sure if PNGs would have the same issue if ran through PNGCrush or not. These "optimizers" use cheats and exploits to get file size low sometimes, I bet that's the issue here.
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