I have a dedicated pfSense box. The lan port feeds into a basic 8 port switch which supports a LinkSys WRT 1900AC access point, an old DC (DC1), and an eSXI 5.5 box.
ESXI is running a new DC (DC2) that used to be physical, but was virtualized.
I hope that generic graphic makes sense. Anyhow, my AP can authenticate against DC1 without any problems however I cannot get it to authenticate against DC2. All the services and firewall settings are setup correctly. This machine worked fine when it was physical. Also I have tested other services (my kids minecraft server was running on it for a while) and they are accessible from the WAN side of the pfSense box so I know I have connectivity.
I was thinking maybe I needed to connect the AP to the second ESXI ethernet port maybe?? I am an ESXI novice so any direction would be greatly appreciated. And if it helps, both the pfSense and ESXI boxes are running on Dell PowerEdge R210 servers. ESXI has 16GB of RAM and the pfSense has 8GB.