Mastering Windows Privilege Escalation

Introduction

Privilege escalation on Windows machines often stems from misconfigured user privileges. One notable example is the assignment of the SeImpersonatePrivilege to user accounts running critical services like IIS or MSSQL. This setup creates a direct pathway for attackers to elevate privileges, making it an essential check for anyone who gains Remote Code Execution (RCE) through SQL exploitation or web applications due to the high likelihood of these accounts possessing this powerful privilege.

Understanding SeImpersonatePrivilege

The SeImpersonatePrivilege allows a process to adopt another user's security context, which is crucial for legitimate operations but also a major risk for system compromise. This privilege is particularly dangerous because it enables the impersonation of the SYSTEM account, allowing direct escalation from RCE to full system compromise.

Before attempting to exploit this privilege, it is crucial to confirm whether it is enabled on the target system. Use the following command:

whoami /priv

If SeImpersonatePrivilege is listed as "Enabled," it indicates potential vulnerability.

Juicy Potato

The Juicy Potato exploit leverages the Component Object Model (COM), a Microsoft framework that supports inter-process communication and dynamic object creation. This operates much the same way as SO files on Linux and DLL files on Windows, except that it allows for them to be loaded remotely.

Juicy Potato creates a rogue COM server that interacts with a user account with SeImpersonatePrivilege to impersonate the SYSTEM account and execute arbitrary code:

JuicyPotato.exe -l 1337 -p c:\windows\system32\cmd.exe -a "/c whoami > c:\	emp\priv.txt" -t *

This specifies the listening port (-l 1337) for the rogue COM server, the path to the executable to run (-p), and the command line arguments to execute (-a). The -t * flag indicates that the exploit may use any suitable COM object class ID (CLSID) available.

Juicy Potato is primarily effective on Windows versions prior to Windows 10 and Windows Server 2016, where later updates have mitigated some of the underlying vulnerabilities. For more details, see the Juicy Potato GitHub page.

Rogue Potato

An evolution of Juicy Potato, the Rogue Potato exploit uses advanced token manipulation and NTLM relay techniques to elevate privileges:

RoguePotato.exe -r 127.0.0.1 -e "cmd.exe /c net user rogue admin /add" -l 1337

This sets up a server to listen for incoming NTLM tokens (-l 1337), specifies the relay target address (-r 127.0.0.1), and the command to execute (-e), adding a new admin user.

Rogue Potato is effective on Windows 10 and Windows Server 2016 and later, addressing some of the mitigations that affect Juicy Potato. Explore this further on the Rogue Potato GitHub page.

PrintSpoofer

Another technique is the PrintSpoofer exploit, which targets the Windows Print Spooler service to escalate the executing user's privileges to SYSTEM:

PrintSpoofer.exe -i -c cmd

Running the exploit interactively (-i) and specifying the command to execute (-c cmd) opens a command prompt with SYSTEM privileges. PrintSpoofer works by abusing the Print Spooler service's ability to run with system privileges and exploiting improper handling of advanced printing features.

This exploit is particularly effective on Windows versions up to and including Windows 10 version 2004, where subsequent patches have started to close this vulnerability. Further details can be found on the PrintSpoofer GitHub page.

Further Reading

For an in-depth discussion on these topics, including tutorials and examples, the HackTricks article on SeImpersonatePrivilege is a comprehensive resource detailing the exploits mentioned above.

Conclusion

This exploration of SeImpersonatePrivilege exploitation techniques highlights the significant opportunities that these vulnerabilities present for penetration testers. As one of the more commonly misconfigured privileges in Windows environments, SeImpersonatePrivilege often represents low-hanging fruit for attackers.

By mastering these techniques, penetration testers can effectively identify and exploit such vulnerabilities, enabling them to escalate privileges efficiently during assessments. This capability is critical not only for demonstrating potential attack paths in security audits but also for understanding how to anticipate and mitigate similar tactics used by malicious actors.

Regularly checking for and exploiting SeImpersonatePrivilege should be a staple in any penetration tester's toolkit. Stay sharp, continuously hone your skills, and keep pushing the boundaries of what's possible in your penetration testing endeavors.