I have a problem with strange behavior of IIS 8.5. The server hosts Exchange with configured SSL of course. The problem started when I replaced an intermediate certificate of StartCom from SHA1 to SHA2. It works on all my resources but not only this Exchange server. What I did: i've removed the old SHA1 intermediate certificate from the cert store, downloaded proper certificate from StartСom, rebinded web sites and rebooted the server. It did not help. When I open the web site on the server it works, but remotely the server has kept sending the old sertficate SHA1. I checked that there is no any certificate with this serial number on the server. I dug the internet and found similar problem IIS sends incorrect intermediate SSL certificate The guy had the same issue. But unfortunately, no one solution didn't help me. My server returns wrong intermediate certificate which doesn't exist on the server even. Somebody know if there is a way to get IIS to build cert chain with specific certificates? Thanks.
Does the new Certificate have a intermediate ? if so make sure you have it import correct.
Go in Exchange Admin Center then Server and Certificates tab then Edit the Services need. (IIS)
Was your SSL certificate actually signed by this new intermediate cert? If you haven't rekeyed the certificate with your CA, it will still have the old intermediate in it's chain.
If you did generate a new certificate you may need to reboot the IIS server. I've seen where IIS cache's the certificate chain and rebooting fixes the issue.