Printing across site-to-site OpenVPN tunnel

  • We have setup a data center server and some workstations with a pfSense instance running in front of it. We have 2 remote locations each running an SG-3100.

    We have successfully setup a site-to-site OpenVPN tunnel to each location following the documents provided by pfSense.

    Traffic passes between sites without issues (ICMP, web traffic on ports 80 and 443, etc.).

    Each site has an IP printer which we need to connect to the server to allow the virtual workstations to print to the appropriate local printer as well as monitoring the print queues. The goal is to have the printers connected to the server and all clients (whether virtual in the data center or at the local sites).

    We've been able to successfully connect the printers via IP. The problem is, when we submit a print job, it hangs and eventually fails. I'm about to start wireshark troubleshooting but wanted to ask the community if they've seen anything like this whereby printing across the OpenVPN starts but errors out without any kind of specific error other than "printing failed."

    Server: Windows Server 2019
    Clients: Windows 10 1903
    Printers: Ricoh Lanier MP C305 and HP Color LaserJet MFP M281fdw
    Client pfSense: SG-3100 with 2.4.4 p3
    Server pfSense: VM in Vultr running 2.4.4 p3

    OpenVPN setup using

    Thank you in advance for your thoughts.

  • Also, local IP printing to each of the printers works as expected.

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