understand how ADFS & Web Proxy servers work. I'm having an issue getting a standard SSL issued to work for the configuration of the ADFS and then the Web Proxy. I'm assuming I need to generate a CSR from the ADFS server at
a minimum of 2048.
How do I generate the CSR for the ADFS domain ss0.contoso.org?
SSL / HTTPS* Active Directory Federation Services (ADFS)
1) flow chart of your device chain
2) how exactly you generated your CSR + cert
3) where exactly you've setup your cert (device in chain)
4) exact error you're seeing
5) before any of this will work, you must fix ss0.contoso.org where it resolves publicly, as currently this host returns no IP.
Note: SSL certs pin to hostnames returning IPs. You must fix #5 before you can make any progress.... unless all this is a Private CA setup, which will always cause you problem. Based on your description above, you must use a host that resolves + a cert generated with a public issuance chain.
https://LetsEncrypt.org provides free certs, SNI + Wildcard.