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I am trying to get a computer to run some software from a remote location. In order for the software to run it has to be listed in the license manager of this software with an IP address and Mac Address.

We have our office LAN - 192.168.1.1/24

I have my Home LAN - 192.168.5.1/24

Then we have the VPN LAN - 192.168.100.1/24

I have this computer (Surface Pro) connected to the L2TP VPN using the standard VPN setup on windows 10.

When I do ipconfig /all on the surface pro while it is connected to the VPN I see the 192.168.100.1 IP address it is assigned, but it is also showing the wireless adapter connected to my home network with the IP address 192.168.5.181.

When I attempt to add this computer to the license manager with IP it errors out. When I add the mac address, it add it to the list with unknown IP.

When I try and launch the software with the mac address added to the license manager (Hosted on the server in the office), I get an error saying it could not connect to the SQL DB. When I attempt to launch the software without the MAC address added to the license manager, the software prompts me with the computer name, IP, and MAC address and tells me to go add this computer to the license manager (As it should). BUT the IP address the software is giving me to go add it to the license manager is my 192.168.5.181 IP address, and not the 192.168.100.1 it should be using since it is connected through the VPN.

I know the surface is talking to the server, because I get different messages when attempting to launch the software if I have the mac address in the license manager vs when I don't. I have tried adding the 192.168.100.1 ip with its Mac address to the arp table of the server using arp -s, but that has not resolved the issue.

Any help resolving this will be GREATLY appreciated.

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  • Sounds like crap software - and yoy should speak to the vendor. It almost sounds like the software requires both devices be in the same subnet to work. A wild guess - and a lot of hassle - using a VPN based on a tap rather then tun driver might work - along with all the routing changes and inefficiencies it brings.
    – davidgo
    Commented Aug 29, 2020 at 21:39
  • I am not sure what you mean by using a VPN based on a tap rather then tun driver. Could you elaborate on this? Also, it is the vendor, and they do ONLY want devices on the local subnet to work. We have called them about this and they are unwilling to change it. I am trying to work around this issue...
    – Lzypenguin
    Commented Aug 29, 2020 at 21:42
  • Another thought - from your post you certainly seem to know enough about networks - but have you checked the netmasks are not overlapping and that NAT is not creeping in anywhere.
    – davidgo
    Commented Aug 29, 2020 at 21:42
  • @davidgo I have, and none of that is the issue. This software is supposed to only be ran from within the same subnet, and I am trying to work around that, which is the issue. The one thing I have thought about doing is deleting the active route for my local network using: route delete 0.0.0.0 192.168.5.1, so that all traffic is forced to go over the VPN, and then adding the server IP to the surface pro's arp table.
    – Lzypenguin
    Commented Aug 29, 2020 at 21:46
  • I'm a Linux, not Windows person, so I can only advise in general terms for Windows. TUN interfaces are point-to-point interfaces and routed. TAP interfaces create a single large virtual LAN - think of it as creating a 2 port switch with each port in a different location. With the restriction of on-the-same-lan you may well need to set up this latter type if VPN. I'm pretty sure OpenVPN can work with TAP drivers on Windows.
    – davidgo
    Commented Aug 29, 2020 at 21:49

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