Dear Jeremy, I have the same problem with my website.
I tried installing JetPack but have been facing this issue since day one.
Error Details: The Jetpack server was unable to communicate with your site [HTTP 404]. Ask your web host if they allow connections from WordPress.com. If you need further assistance, contact Jetpack Support: http://jetpack.me/support/
My website is : http://www.rahulkcjain.com
Please help me in the solving the above issue.
Thanks in advance.