Trouble with WinRM

I am setting up a brand new environment with Windows Server 2019 Standard and Datacenter CORE install (No GUI). I am trying to reduce the attack surface. I have setup several servers but one keeps denying access. This server worked for a time but now refuses all Windows Admin Server connections indicating that i need to run winrm quickconfig. I checked netstat and the service is listening on 5985 as it should but when i test from my management server using Test-WSMan it cannot connect. My firewall has been disabled and i have no antivirus installed at the moment. I am not seeing anything in the logs that im checking but I am not sure the best way to troubleshoot this problem. Any help would be greatly appreciated.