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For testing purposes of a logging solution, I would like to simulate an attack by using Metasploit against a Windows 7 / Windows 2016 server. However, I am struggling to find a reliable exploit that actually spawns a root shell on the victim machine.

Initially, I tried to identify a reliable MSF module to be used during the exploit. I selected windows/http/icecast_header as it seems to be more or less independent of the underlying OS version (Win 7 vs. Win 2016). Thus, I installed the vulnerable Icecast version on the victim machine and configured the MSF module. However, as stated before, I am getting a Exploit completed, but no session was created.. On the victim machine, the server simply crashes and I am getting a message "Icecast2win MFC Application has stopped working".

Thus, my actual question is: Do you know of a reliable MSF mdoule that works on Windows 7 / 2016 that I can use for testing purposes?

Thanks, André

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  • You are looking for an exploit but you should be looking for something exploitable. Are you using a vulnerable version of Win7?
    – schroeder
    Oct 18, 2020 at 7:42

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You will have better luck with Windows 7 than Server 2016. The go-to is MS17-010. You would need to enable SMBv1 and ensure that it is not patched for that version. You can ensure that it's vulnerable first with Metasploit or nmap (nmap target -p445 --script=smb-vuln-ms17-010).

For Server 2016, I would recommend looking at a web vulnerability. For instance, you can install Tomcat and then use Metasploit to upload a malicious WAR file. This would produce a shell in the context of the user running the web service.

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