Once again I tried to upload an Illustrator file (exported as a .jpg) with absolutely no luck. Jessican also had the same problem over the weekend. The work around seems to be you find another image that will load and cut and paste your image over the top of the original resave without changing the name and Ta-Da it works.
But why is that? So I called upon my computer genuis and asked him. When he looked at the files he noticed that the file that will load has a JFIF added to the name. When I was looking up how to make all my files say that I came across the following site
Graphics Formats Explained
How cool..nice neat explanation but no real solution yet for the other problem.