Brian, your image is too large. You'll see the "maximum size" specs near the "Browse" or attachment window -- 400 (width) x 600 (height). A larger image simply won't (can't) attach.
Resize your image and try again. If that doesn't help, we'll go to Plan B. I'll start thinking of one.
Make sure, too, that your image has an acceptable file extension. They are: gif jpg txt zip jpeg xls (psd from Photoshop won't work -- resave such an image in another format.)
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