Somewhere along the line, I went down the rabbit hole trying to avoid a SAN certificate and get away with a single certificate that would cover the RDWeb/Gateway/host of the single-server deployment of Remote Desktop Services/RDWeb/Gateway/Session Host (
Now, I have no idea how I changed the Remote Computer parameter to
remote.contoso.com, which is the same as the gateway, but cannot be resolved/proxied. **
What's weird is that I'm sure I've fixed this, but after a reboot, it seems to not be persisting.
Looking for canonical ways that this could be changed (Powershell/Registry entr(ies), configuration file(s), etc.) with the end-game being to get it back to "normal": where a simple QuickCollection for Remote Desktop sessions would take the fully-qualified hostname of the Session Host and auto-generate that as the Remote Computer in Remote Desktop shortcut/file on the RDWeb website.
** or its possibly a hairpin NAT issue; not 100% why the single server stack cannot proxy onto itself as that hostname, because I do have split DNS enabled, so you can from another host RDP to
remote.contoso.com from within the same network as
RDS01. Perhaps it's some loopback safety measure?