Hello Josh,
Being unable to contact the server usually means that the server where the OutSystems platform is installed can’t reach the AD server. If you’re running an on prem server you can ask your network guys to check the connection from within the server.
However, if you’re running cloud, you’ll need to send an email to our support asking to open a port to your AD server.
I hope this helps and it’s great to see the way you’re trying to use the platform.
Good luck.