Its fairly easy to setup https functionality when you’re running an Apache web server however when trying to do the same thing in IIS you will encounter the problem of generating a certificate and having to rely on a Certification Authority such as Verisign or your own certification server to have the certificate authorised.
This problem is easily solved with Microsoft SelfSSL utility, which can be downloaded here. It will only install under XP or Windows 2003 however you can copy the SelfSSL.exe file directly into a 2000 computer and run it without a problem.
A typical command option you can run (this will give you a certificate valid for 120 days) is:
selfssl.exe /N:CN=(computername) /K:1024 /V:120 /S:1
And thats it! This will take care of the certificate generation and installation. Watch out if you are running multiple Web Sites under the one server as you will have to fiddle with the /s tag to point the SSL certificate in the right direction.