Setting up LetsEnccrypt on IIS 6.x Windows Server 2003

  1. Yes - review this article https://www.linkedin.com/pulse/lets-encrypt-part-2-3-repurposing-clients-making-things-andrei-hawke

  2. You don't have to do anything - however there are easy ways of doing things and hard ways. Review the article above.

  3. I would recommend not using the CSRs from microsoft as they tend to have a whole of extra fields and properties which are specific for microsoft.

Shame there's not a semi-automated way to do this with letsencrypt.org, much like I'd been doing with Godaddy (show I control the site with DNS or by putting a file on the web site, submit the CSR, get back a cert with any intermediate certs, install them. Not very complicated actually. I wouldn't mind doing that every 3 months until I moved to 2016?

That is exactly how some of the clients work.

Review these clients:

Andrei