This sounds like a job for an approach like [0]! Reminds me of [1].
0. http://lcamtuf.blogspot.fr/2014/11/pulling-jpegs-out-of-thin..., http://lcamtuf.coredump.cx/afl/, american fuzzy lop
1. http://news.cornell.edu/stories/2015/03/images-fool-computer..., Images that fool computer vision