OSEP study materials
OSEP study resources

OSEP case studies

OSEP · Put your knowledge to work in context.

The OffSec Experienced Penetration Tester (OSEP) credential - historically tied to the PEN-300 course track - is an advanced, hands-on certification aimed at practitioners who already operate comfortably in Windows and Linux environments and want to demonstrate tradecraft beyond basic exploitation: phishing and client-side delivery, evading antivirus and EDR controls, bypassing application whitelisting, escalating privileges in Active Directory, moving laterally, and sustaining post-exploitation access on Linux hosts. Candidates are typically red teamers, senior penetration testers, or security engineers whose day job involves operating against defended networks rather than isolated vulnerable boxes. The OSEP case studies are 5 cases and about 3,816 words.

1

Valid Password, Number Matching, and a 48-Hour Window

During an assumed-breach engagement you recover a cleartext password for m.santos (Finance) from an infostealer log. The tenant enforces MFA with number matching, and Conditional Access requires MFA for all users but does not require compliant or hybrid-joined devices.

733 words, about 4 min
2

Beacon on a Host With Defender ASR and Falcon

You have local admin on a Windows 11 23H2 workstation. Defender is active with cloud-delivered protection, ASR rules in block mode (including LSASS credential theft), and tamper protection enabled.

779 words, about 4 min
3

GenericAll, Shadow Credentials, and a Service Account DA

BloodHound shows your controlled user helpdesk1 has GenericAll on user j.reid. j.reid is a member of Tier1-Admin, which has AdminTo on server FS01.

739 words, about 4 min
4

Sudo Rsync and a Backup Job You Cannot Break

You have a shell as svc-backup on a CentOS 7 host. sudo -l shows (root) NOPASSWD: /usr/bin/rsync and nothing else.

717 words, about 4 min
5

Relay Target Selection When ESC8 and SMB Signing Disagree

You have a foothold on workstation WS-042 as a low-privileged domain user. SMB signing is disabled on member servers FS01 and FS02, but required on all domain controllers.

848 words, about 4 min