Jeremy,
Thanks for the feedback. The images you're seeing were being forced via a script in my functions file. I wasn't sure how long it might be before a fix was found so I went looking for other options.
If you'll notice - the images that were pulled in is an image from my sidebar - not the actual post as well.
It seems Jetpack is ignoring any images in the post itself.
I've pulled the code from my functions file so you can get a better look at what's happening "out of the box."