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.