Hi there,
I’m sorry to hear you’ve run into issues.
I don’t have a link to your site so I can’t test to make certain, bit I suspect that your server is unable to make verified outgoing HTTPS requests to https://jetpack.wordpress.com/.
Jetpack tries to detect that inability and instead make outgoing HTTP requests to http://jetpack.wordpress.com/. These HTTP requests are insecure (especially during the initial connection), so Jetpack tries to do HTTPS requests, but on some servers this is impossible.
Jetpack doesn’t realize that the particular type of failure with HTTPS requests your server is having should indicate that Jetpack needs to fall back to HTTP requests. Jetpack falls back to HTTP for several other types of failures, but it doesn’t know about this type of failure. We’ll work on getting that fixed for a future version of Jetpack.
Jetpack should handle this failure more gracefully. In the meantime, though, you can hopefully fix the root of the issue and stop that failure from happening in the first place.
It sounds like cURL’s SSL certificate bundle is either missing or out of date on your server.
If you’re running PHP 5.3.7 or later, you can try the following to get a new copy. For earlier versions of PHP, the following will not work.
1. Download the PEM certificates file from here: http://curl.haxx.se/docs/caextract.html and save it someplace useful.
2. Add to your site’s php.ini file the following line (replacing “C:/path/to/” with the actual path to the file you saved in step #1):
curl.cainfo=C:/path/to/cacert.pem
3. After saving your php.ini file, you probably have to restart your webserver (IIS).
Note: you can figure out where your php.ini file is (step #1.5) by creating a PHP file on your server that has only the following code:
phpinfo();
Browse to that file’s URL in your web browser, and you should see information about your site’s PHP configuration, including the location of your php.ini file. While this might not be the best way to address the lack of cURL certificates, it should solve the problem.
I hope this helps. Please let us know if you need any more help.