Thank you everyone for the input. I resolved the issue, my setup was right i just had to allow Port 8100 in the VM firewall. Worked it out by using wireshark For those wondering what i was setting up it was a cloud solution for an onprem application that pushes a print to a onprem server. Everytime the main site went down the other sites couldn't access the Server on the VPN. I recreated it with a Azure to Meraki VPN that then pushed an application print to an Azure VM that had an IIS server connecting to a web server, running as a Print Proxy Server. it then pushes the print to Universal print and back to a site. This also allowed the application to be installed on PCs from Edge on the VM public IP. Now each site runs individually and access the same functions in the cloud.
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