Dave, have you checked your image properties? It has to conform to these:
Allowed file types: txt, doc, pdf, jpg, gif, mpg, png
Maximum attachment size allowed: 5000 KB, per post: 10
I'll test and see if I can upload... Nope, I get
Error 500 - Internal server error
An internal server error has occured!
Please try again later.
Internal server error
Your Web server encountered an unexpected condition that prevented it from fulfilling the request by the client (e.g. your Web browser or our CheckUpDown robot) for access to the requested URL.
This is a 'catch-all' error generated by your Web server. Basically something has gone wrong, but the server can not be more specific about the error condition in its response to the client. In addition to the 500 error notified back to the client, the Web server should generate some kind of internal error log which gives more details of what went wrong. It is up to the operators of your Web server site to locate and analyse these logs.