"Let’s Encrypt is a free, automated, and open certificate authority brought to you by the non-profit Internet Security Research Group (ISRG)." Which handles the renewals going forward automatically.

  1. Install Certify The Web on the server you would like SSL on.
  2. Go through the guide when it opens, use a real email address.
  3. New Certificate
  4. Select the site you want SSL on
  5. Request Certificate
  6. Setup autorenew

We'll set the SSL renew for 14 days before it expires and the also set PRTG to alert us if the certificate get's below 13 days.  This should be a great solution and we'll know if it's ever not working with PRTG monitoring it.