I have a single domain that I would like to setup encryption for…I am using two servers that are load balanced. My question is, I would need to setup Let’Encrypt on both servers, right? I am using Windows 2012 R2 and plan to use Letsencrypt Win Simple client.
If you have an actual load balancing server that sits in front of the two servers, where only the load balancer has an A record in DNS, then you would only need to setup Let’s Encrypt on that server. (Unless you also want to use it to secure the connection between the load balancer and two origin servers, in which case you’d need it for all three.)
If you are using DNS round robin “load balancing”, such that both servers have A records listening on the domain with no intermediary server, then yes, you will need to setup SSL and certificates for both.