In reply to Justin Lewis.

Hi! I work on the Jetpack team, and I'd be happy to help you figure this out!

Can you please use Jetpack's Debugger module to send us some more information about your site?

Go to the Jetpack page in your dashboard.
Click on the Debug link appearing at the bottom of the page.
Click the link that says "click here to contact Jetpack support."
Fill in the description box and your name and email address.
Click the "Contact Support" button to send us the debug results privately. It's best not to post this information here, as it contains private details about your site.

Thanks!