Started encountering the same issue a few days ago, after probably 6+ months of a working setup (OS X & brew-installed openvpn). After significant debugging, I believe it’s something to do with the routing that gets applied to vpn (utun*) interfaces. I don’t know exactly how to solve it, so like others in this post I’m swapping to using VM-based attack boxes from now (which is probably what I should have always been using, anyway).
It is a very strange error indeed. I use macOS 12 Monterey and I faced a similar issue. In my case, whenever I connect to the VPN using OpenVPN, I am able to ping the server but loose access to every other thing on the internet outside the private network.
I solved this by renewing DHCP lease following these steps:
Go to System Preferences → Go to Network
In Network, click Advanced on the bottom right
Click on TCP/IP tab
Click Renew DHCP Lease button. Click Ok…then click Apply to apply the settings.
From here on, I have access to the internet and things work as they should. Unfortunately I have to do this everytime I open a VPN connection to HTB.
I know this is an old thread but I just wanted to say thank you, this worked for me. One thing to note is that you need to renew the DHCP lease while connected to the VPN.
On macOS Ventura, because of the new System Settings app the exact steps to get to those settings are a little different, so I’ll include them here in case anyone has an issue:’
Go to the ‘Wi-Fi’ tab
Click ‘Details…’ next to the network you’re connected to
Click the ‘TCP/IP’ tab (if it isn’t already there)
