CPENT & advanced penetration testing mentorship
For people who already test systems and want to go further: multi-network pivoting, Active Directory, web and binary exploitation, and reports a client can act on. This track prepares you for EC-Council CPENT and OSCP-style practical exams. These are certifications you work towards here; I mentor from my own penetration testing work and CEH v12, not as a CPENT or OSCP holder.
Independent mentorship and coaching. Not official, authorised or affiliated training from EC-Council, OffSec, CompTIA or any other certification body. Exams, vouchers and official courseware are bought from the certification body directly.
Who this track is for
Working pentesters who want a structured path to a practical certification
Security engineers and SOC analysts moving into offensive roles
CEH holders ready for long, hands-on exams
CPENT & advanced pentesting: syllabus breakdown
- MODULE 01
Scoping & methodology
Rules of engagement, written authorisation and a repeatable testing methodology.
- MODULE 02
Network & perimeter testing
External and internal networks, perimeter devices, pivoting and double pivoting across segments.
- MODULE 03
Active Directory & privilege escalation
Windows and Linux privilege escalation and common Active Directory attack paths.
- MODULE 04
Web application testing
Manual testing beyond scanners: access control, injection and business logic.
- MODULE 05
Wireless, IoT, OT & cloud
The specialist areas covered by CPENT, practised in lab environments.
- MODULE 06
Binary analysis & exploitation
Reading binaries, basic exploit development and adapting public exploits safely.
- MODULE 07
Reporting
Evidence, risk ratings and remediation written up as a professional penetration test report.
Indicative week-by-week plan
Indicative only, not a fixed schedule. Contact me to plan your mentoring around your background, weekly study hours and exam date.
- Weeks 1–2SPRINTMethodology, enumeration and note-takingTimed boxes on Hack The Box and TryHackMe
- Weeks 3–4SPRINTPrivilege escalation, Windows and LinuxPrivilege escalation lab series
- Weeks 5–6SPRINTActive Directory attack pathsAn AD lab you build and attack yourself
- Weeks 7–8SPRINTPivoting and multi-network environmentsMulti-host networks with pivoting
- Weeks 9–10SPRINTWeb, binary and specialist areasWeb labs and beginner binary exploitation
- Final weeksSPRINTFull mock exam and reportA long timed lab followed by a full written report, reviewed together
All hands-on work happens strictly on authorized lab platforms (TryHackMe, Hack The Box, or personal lab).
CPENT & advanced pentesting: frequently asked
Do you hold CPENT or OSCP?
No. I hold CEH v12. This track prepares you for CPENT and OSCP-style exams through hands-on practice and report reviews; it doesn't come from an official instructor for either.
Is this official EC-Council CPENT training?
No. It's independent mentorship, not official, authorised or affiliated EC-Council training.
Where do the labs run?
On Hack The Box, TryHackMe, other legal lab platforms and environments you build yourself. Never on systems you don't have permission to test.
What level should I be at before starting?
Comfortable with Linux, networking and basic exploitation. If you're not there yet, the Foundations or CEH track is the better start.
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