Figured I'd take up a few unsolved cases...
1. How many images were you trying to send through email? Most mail servers will not allow files or file batches bigger than 20-30MB to be sent at one time, if you happened to be sending 39 images, that would definitely explain the error as an image with a nice resolution can be 3-5 MB.
2 As far as the file association, if it is really a JPEG image it should open in Windows Photo Gallery... I would check to see if you can open other JPEGs on your computer.