I have been stumbling with this for over 6 months. I found some very old information about this setup but nothing recent and certify has released a bunch of updates in the past 6 months. I can add a single cert without any problems but for some reason windows will not pass the correct binded cert after I have more than 2. Has anyone found a solution to add 5+ certs on the same ip address and server. I am running on an azure windows 2016 server. 14gb/4 core.
And yes, I have checked the Require server name indication on each binding.
Well, I guess I just needed to spend more time working on this. I went through all settings again and then I restarted my server. With my old Dell server a restart could take as long as 15-30 minutes so I rarely did them. With my Azure server it is back up and running within 20 seconds. God I love SSDs Anyways, after a restart and reconfiguring, it works perfectly. I now have 8 websites with SSL running on the server.
It is pretty hilarious when restart computer causes a problem for me. I have been doing tech support for over a decade now and it solves 98% of the problems my clients contact me about. Unless I am deep in a project I always restart first. What is also interesting is that after restart I added 5 of the 8 websites and I did not need another restart to get them to go active, so I have no idea what was causing the issue. For some reason my server was getting confused and saying all sites had the same SSL cert. I had the same problem on my former server so I assumed it was an issue with Windows/IIS. I am so happy this is resolved.
Anyways, after a restart and reconfiguring, it works perfectly. I now have 8 websites with SSL running on the server.