in a Windows environment, Let's Encrypt does not have very good support. There are very good ACME clients (ACMESharp, etc) for windows that allow doing http-01

in a Windows environment, Let's Encrypt does not have very good support. There are very good ACME clients (ACMESharp, etc) for windows that allow doing http-01 and dns-01 certificate issuance. Additionally, there is IIS integration (letsencrypt-win-simple) with the stuff you would expect (cert generation for all or specific sites, automatic renewal, etc). Basically the only thing Windows doesn't have is official support in the Certbot client.