I actually gave up using JAMF remote some time back. It is super picky about DNS stuff and with 90% of our work force on VPN it was not worth dealing with. From what I understand it does not check with JAMF Pro/Cloud to get the current device IP address and relies on possibly out dated DNS records so the majority of our JAMF Remote connection never got to their intended destination.
I have also heard that JAMF remote is more or less technical debt at this point. Much like JAMF Recon and JAMF imaging, the JAMF software suite is loaded with stuff they do not maintain and that apple has stopped from working.