I am having a similar issue. When I go to the Jetpack page in my admin panel there is a red message which says:
Error Details: The Jetpack server was unable to communicate with your site https://boxtoninc.com [IXR -32300: transport error: http_request_failed cURL error 60: SSL certificate problem: unable to get local issuer certificate]
If I try and hit connect, it redirects me to: /wp-admin/&from=landing-page-top
which is a 404 error.
I recently installed SSL on my site as well and went from http to https
