I have an unpatched Windows XP Home VM, a Kali 2019.2 VM and an old Kali 2016 VM. Using Metasploit's ms08_067_netapi module, I'm able to successfully get a reverse shell but only on the old Kali VM.

I'm trying to get the same reverse shell on Kali 2019.2, but it is not working. However, I've been able to get a meterpreter bind shell running from the Win XP VM to the 2019.2 VM using the same exploit.

I have done the following with IPTABLES to completely clear everything:

sudo iptables -F
sudo iptables -P INPUT ACCEPT
sudo iptables -P FORWARD ACCEPT
sudo iptables -P OUTPUT ACCEPT

But I still can't catch the reverse shell. Metasploit reports:

[ * ] Exploit completed, but no session was created.

Lastly, I have been able to catch a reverse shell from the Windows XP machine to the 2019.2 VM by creating a windows/meterpreter/reverse_tcp executable file using msfvenom and running it on the target Win XP machine (and catching it on the 2019.2 Kali VM using multi/handler), but I still cannot get a reverse shell from Metasploit's ms08_067_netapi module.

Any insight on this bug would be greatly appreciated!

  • What happens when you set VERBOSE true in Metasploit and run MS08-67 again? – AbsoZed Jun 26 '19 at 20:17
  • The same thing, started handler on 4444,auto detecting the target, fingerprint Win XP SP 0/1 English, targeting Windows XP SP0/SP1 universal, attempting vulnerability, exploit completed no session created. It's pretty much what the 2016 box's msf says, minus the stager and meterpreter shell. – PenTest Jun 27 '19 at 0:54
  • Are you utilizing the same payloads? Maybe try altering that to see if any one payload works. It's possible they have changed between MSF versions. – AbsoZed Jun 27 '19 at 14:12
  • As mentioned above windows/meterpreter/reverse_tcp is the one I'm trying to get to work on the 2019.2 box, and it works on the 2016 box. On the 2019.2 box I am able to successfully use windows/meterpreter/bind_tcp – PenTest Jun 27 '19 at 15:01
  • Just found that generic/shell_reverse_tcp works – PenTest Jun 27 '19 at 15:27

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