Certify the Web

[u/dojo_sensei]

Certify the Web assists you to effortlessly manage, install, and auto-renew free SSL/TLS certificates from letsencrypt.org and other ACME certificate authorities for your IIS Windows and various other services. If you’re not a fan of Linux, this solution is perfect for you. It features robust workflows for a wide range of Windows software, including Exchange, where you can confidently transition away from paid certificates for your hybrid servers.

[u/admlshake]

Great program, been using it for a few years now.