Oh, okay. I'll try uploading an image of comparable size and see what happens.
Well, as you can see, the image uploaded fine. It's 638x450 and 63KB in jpg format.
Try changing the format extension from jpeg to jpg and see if that helps. The jpeg extension can sometimes prove a tad tricky whereas jpg is more universally recognized.
Daniel, I am in Windows 10 1607 (using Firefox) so I don't think changing OSs is going to make much difference... still, maybe worth a try.
Send me an image which failed to upload as an email attachment and I'll try uploading from here. This will at least tell us if it's definitely a problem your end or some sort of problem with the image.
What tool are you using to create the screenshots?
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