We have a dev portal 11.1 that has a 2 system multi-machine site connected to it. Only one of the ArcGIS Servers show up in Portal > Organization > Settings > Server, but both servers are being accessed through the Web Adaptor. It has been working fine since I started on the portal. We just upgraded both the Portal and ArcGIS Servers to 11.3 and now the server that is not listed as a federated server is having authentication problems. When both servers are operational, users will get timeouts when trying to access the services from the rest endpoint. But if I turn off ArcGIS Server on the second server then everything works correctly.
I have looked online to try and find information on having a multi-machine site connected to a Portal, but I have not been able to find anything. Do you have any suggestions for how to get the second server from the multi-machine site to fully authenticate with Portal?