SSL certificates are a necessity, and if you take a few minutes you can have one for free thanks to LetsEncrypt and CertifyTheWeb.

Note: We use an Azure VM for our Rock server, and Cloudflare for our DNS, but these steps should still apply to most setups where you have an admin account on a Windows Server.

Process

✔ Generate SSL certificate via Certify

1. Log in to your server using Remote Desktop.
2. Download Certify onto your server and install.
3. Run the Certify app on the server. 
4. Get a certificate from LetsEncrypt via Certify. Follow the Certify guide for more details.
   For your reference, I have used the following settings for our server:
• Certificate Domains
• Select the IIS website that runs Rock (for us it was just Default Web Site)
• We have one domain (e.g. ourwebsite.com) and use 2 subdomains (e.g. rock.ourwebsite.com and my.ourwebsite.com) for Rock. Because of this, I use a wildcard for the domain:  *.ourwebsite.com
• 
  
• Authorization
• Domain Match - I used the same wildcard for the domain as in the previous step: *.ourwebsite.com
• Challenge Type - I used dns-01
• DNS Update Method - Because we use Cloudlfare, I used Cloudflare DNS API
• 
  
• Deployment
• Deployment Mode: Single Site
• Binding Add/Update: Add or Update https bindings as required
• Matching any of:
  - Existing binding hostname matches certificate domains
  - Binding hostname not specified
• IIS Binding Settings: Auto create/update IIS bindings
• 
  

🌎 IIS Manager

1. Open IIS Manager on your Windows Server.
2. Select the Site that you chose above (e.g. Default Web Site)
3. Edit the Site bindings
4. Edit your https binding. (If you don't have one, just click Add)
   Ours has the following settings
• Type: https
• IP address: All Unassigned
• Port: 443
• Host name: blank
• SSL certificate: Choose the new Certify SSL certificate
• 
  

☁ Cloudflare Settings (if applicable)

1. SSL: Flexible
2. Always Use HTTPS