Please provide a link to your blog when ever you ask questions in these forums, starting with http://
We need that to be sure you are in the right forum, and often we need to see the blog to provide an accurate answer.
Assuming you have a blog at wordpress.COM,
There have been a number of problems with the pop-up window on the profile page. Be sure you are logged in to your wp.com account and go directly to http://en.gravatar.com/
Also, just because the file is named with a .jpg extension does not mean it is actually a .jpg file. I’ve seen this issue when images are edited or created using MS Paint and the correct type of file type output is not set when the image is saved (but the name was changed to image.jpg) which ends up creating a .bmp file with a .jpg extension.
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