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multiple users from our office (including me) cannot get VPN to work on their Macs. Problem is, that we are successfully connected to the VPN but cannot reach internal servers via IP address. (ie. NAS shares)

On my private linux (Ubuntu) machine it worked from the start without any issue ever since.

In the initial installation of the VPN connection on the system we had to issue a sudo command for it to work:

sudo networksetup -setadditionalroutes "VPN (L2TP)" 192.168.1.20 255.255.255.0 10.2.0.0

I guess it is because the IP the VPN clients get is 10.2.0.x and our servers internally run in the 192.168.1.x subnet.

How do I know we are successfully connected? => Our VPN runs on a Synology NAS and it has a webapp running. It shows that users are connected with the VPN server.

DNS? DNS is set on WLAN or Ethernet to first connect to our internal DNS (192.168.1.15) (which only works when the system is connected to the office network of course; Fallback is 1.1.1.1)

Search domain? We've set that to our ActiveDirectory DNS name, which should resolve ones connected to the VPN. (Same IP as our DNS Server)

I'm not much of a network or hardware guy so I cannot think of anything that should be applied here.

Does anybody of you got an idea of what to try or how to debug this?

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Problem was the static rule. So instead of

sudo networksetup -setadditionalroutes "VPN (L2TP)" 192.168.1.20 255.255.255.0 10.2.0.0

I had to use

sudo networksetup -setadditionalroutes "VPN (L2TP)" 192.168.1.0 255.255.255.0 10.2.0.0

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