I posted a couple of months ago about some ideas I had for integrating Let’s Encrypt certificates with the hosting of Octopus Deploy. The idea was to use many PowerShell scripts with a scheduled release to request a new certificate and install it against the Octopus Server.
I never got to complete this and have since come up with a much easier solution, the reverse proxy. The way a reverse proxy works is by exposing one website as a wrapper around another (internal) website. This is a feature that IIS supports and works well with Octopus Deploy.