This a rather complex way of getting a free certificate and in the meantime Let's Encrypt - Free SSL/TLS Certificates has a much friendlier routine to get a free certificate. If you want to use Let's Encrypt SSL certificates please read Get a free Let’s Encrypt SSL certificate for Access Anywhere and automatically renew it. Here we go! From the Windows Server Essentials Dashboard click Set up Anywhere Access. Choose Click to configure Anywhere Access. Click Next Click Next I already own the domain ‘server-essentials.net’ so I choose that option. Next. My DNS records are already setup. That means that I have a Host A Record for ‘remote.server-essentials.net’ that points to the public IP address of my router that takes care of the Internet connection in my office. As I have already have a certificate I choose ‘I want to use an existing SSL certificate’. That certificate must be in PFX format, any other does not work. We import the SSL certificate in this window. Choose browse to choose the SSL certificate. Choose the SSL certificate. Type your password and click Next The domain is setup with the SSL certificate Now choose which Anywhere Access features you want to enable. In this example I choose to enable Anywhere Access to all users. Click next. Don’t worry if this happens to you and you are sure you opened port 80 and 443 on your router. Sometimes the wizard is a bit silly.