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Ok first of all this is legal and I have it in writing my friend and I are attacking eachother to get better and not break the law.

Setup I have a VMWare image running BT5R3. It uses VMWare's NAT then my network is behind a router using NAT. From there I am VPN tunneled into work which also uses NAT (I believe). I've come to realize that I have only ever run metasploit from the inside or in a lab but never over the internet.

Question
I'm pretty sure with this scenario a reverse payload wouldn't be possible since it requires the machine to connect back to me. Will this work with any payload at all?

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up vote 3 down vote accepted

This won't work with reverse payloads unless you can do portforwarding on the system which is NATing your traffic. Hence it's better to generate a payload which allows you to connect to it rather than a payload which connects back (but if your target is also using NAT, then this becomes obsolete as well). For instance:

shell/bind_tcp

This does give problems if there is a firewall between you and the target. Best thing to do is take away the NAT completely if possible. In your case this seems quite difficult...

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Bind shells don't help much if there is also NAT on the target side. –  buherator Jul 16 '13 at 13:19
    
Yea, you are a bit out of options then. –  Lucas Kauffman Jul 16 '13 at 13:21
    
Our victim servers are honeypots connected directly to the internet so there's no NAT there just from my side. So in this scenario you're saying bind_tcp will work but reverse will not unless I can do port forwarding which is exactly what I was thinking. Thanks Lucas! –  Four_0h_Three Jul 16 '13 at 13:24
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I usually give it about a day before I mark as answer to allow others to chime in. –  Four_0h_Three Jul 16 '13 at 13:26
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