Решил проблему своими силами спустя пару дней поиска.
Решение:
In order to get this working again we had to enable TLS 1.0 on both the WAP and ADFS Server. In particular ADFS (Server) and WAP (Client) had to be enabled. We are likely to see this more often as companies become more aware of threats and attempt to lock down protocols on servers.
Update: We realized that some people may be hesitant to use TLS 1.0 so we did some additional testing. It turns out that this is an issue with .NET Framework 4 not using TLS 1.1 or 1.2. By adding a simple registry key to the WAP Server you can get this functioning with TLS 1.0 disabled and TLS 1.1 or 1.2 enabled.
Location: HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\.NETFramework\v4.0.30319
DWORD Value: SchUseStrongCrypto
Value: 1
Reboot the WAP Server after adding the key and you should be good to go.