The general rule of thumb is that the agent always initiates communication. This is only by memory so it'll be brief. There's a few possible problem sources here, so I'll tackle them one by one. If anyone could provide a pointer, it would be very much appreciated. Is there a requirement to create a certificate on each managed server - I didn't think so? I assumed that the gateway server certificate would be used to sign the communication between the agent and gateway. On the agent managed server I have installed the CA certificate in the trusted root certificates - from the domain CA used to sign the gateway server certificate. But I'm unsure what to match the certificate value against? I have looked to checking the 'ChannelCertificateSerialNumber' in the registry under the location. The nearest reference I can find mentions that this may be an issue with the certificates (which would make sense), but I'm trying to figure out how to validate that I have the correct certs being picked up. When I check the 'operations manager' event log, it's reporting an event ID 21006 The OpsMgr Connector could not connect to :5723.The Error code is 10060L(A connection attempt failed because the connected party did not properly repond after a period of time, or established connection failed becuase connected host has failed to respond.) Please verify there is a network connectivity, the server is running and has registered it's listening port, and there are no firewalls blocking traffic to the destination. I know that communication is working, as I can telnet to port 5723 from the agent to the g/w srver. I have deployed a gateway server into a DMZ, and ran the MOMagent.msi pointing the agent at the FQDN of the gateway server (I placed an entry in the hosts file to map the FQDN to the IP of the gateway server). Would anyone have any guides, or good resources, for troubleshooting agent communication problems between a gateway server and an agent (which is to be managed by said gateway server).

Gateway computer troubleshooting