Debug your IIS server’s certificate issues with Microsoft’s SSL Diagnostics utility

Almost always, installing a new web server certificate for HTTPS (SSL) connections is just a matter of running a configuration wizard, and you are done. But what if things still do not work? Or, you get the wrong certificate from the server, or fail to connect to your IIS web site with HTTPS altogether?

I recently ran into this kind of situation with an older server machine running IIS 6, and because the internal SSL certificate issues are somewhat like a black box in my view, I thought I'd need a helping hand from a suitable tool. Microsoft does provide a little-known utility called SSL Diagnostics, currently at version 1.1.

The utility is executed on the web server in question, and it reports its findings in an easy-to-read fashion. What's nice is that it also gives you hints and tips on how to solve the issues you might be seeing.

If you ever run into trouble with IIS and SSL certificates, give this tool a try. It might save you from a lot of headaches.