#StackBounty: #metasploit #windows-10 #antimalware #virtualbox How to find discrepancy between exploitable and unexploitable VM

Bounty: 50

For several years, I have been setting up VMs with 2-3 year old versions of Windows as well as some additional applications to demonstrate two-stage exploits using Metasploit for educational purposes (more precisely Bachelor-level IT security courses).

This year, I set up a Windows VM from an x86 1803 ISO, installed Firefox 38 and successfully and reproducibly managed to obtain SYSTEM privileges after first using exploit/windows/browser/firefox_smil_uaf (both on its own and via browser_autopwn2) and subsequently exploit/windows/local/appxsvc_hard_link_privesc. This VM works perfectly and I have a restore point from before any attacks that I can go back to and successfully use both exploits.

However, when trying to build a new VM for the course from scratch, I cannot get any of the two exploits to work (Windows Defender detects them as malware every single time). I use the exact same ISO file and installed the exact same software – I kept a folder of all binaries/files as well as a log of every setting that I changed. I tried setting up the Windows VM at least three times now, but every time, Windows Defender detects the exploits, whereas they work flawlessly (i.e., undetected) in my first VM. The VMs have the same amount of memory etc. None of them is connected to the Internet at any time.

How can I find out what difference exists between the VMs (my first, working one, and all the others that I set up based on my notes)? There must be some difference that I missed or accidentally misconfigured. I did not touch any Windows Defender settings in any of the VMs.

A workaround would also be fine for me. I already tried to set the payload(s) to windows/meterpreter/reverse_winhttps and used different encoders, but to no avail in the new VMs. In my first VM, the exploits always work, regardless of the payload or used encoder. Any clues are appreciated.


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