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OffSec OSCP Study Roadmap

PEN-200 / OSCP · 16-week plan · Free

Last updated: September 29, 2026

Progress:
0/16

Domain Weight Distribution

D1: Penetration Testing Fundamentals
15%
D2: Information Gathering & Enumeration
20%
D3: Web Application Attacks
20%
D4: System Exploitation & Privilege Escalation
20%
D5: Active Directory Attacks
15%
D6: Post-Exploitation & Reporting
10%

Week-by-Week Study Plan

Week 1

Domain 1: Pentest methodology, Kali Linux setup, bash scripting, report templates

Week 2

Domain 2: Passive recon (OSINT, Google dorking, Whois, DNS enumeration)

Week 3

Domain 2: Active scanning (Nmap, service enumeration, SMB/SNMP/HTTP)

Week 4

Domain 3: Web attacks. SQL injection (UNION, blind, error-based), sqlmap

Week 5

Domain 3: Web attacks (LFI/RFI, XSS, command injection, file uploads)

Week 6

Domain 4: Windows exploitation (Buffer overflows, public exploits, Metasploit)

Week 7

Domain 4: Windows privilege escalation (Token impersonation, service exploits, unquoted paths)

Week 8

Domain 4: Linux exploitation & privilege escalation (SUID, cron, kernel exploits, capabilities)

Week 9

Domain 5: Active Directory (Enumeration, BloodHound, Kerberoasting, AS-REP roasting)

Week 10

Domain 5: AD lateral movement (Pass-the-hash, pass-the-ticket, Mimikatz, domain persistence)

Week 11

Domain 6: Post-exploitation (Pivoting, port forwarding, SSH tunneling, Chisel/Ligolo)

Week 12

Lab Practice: Work through OSCP lab machines, document methodology

Week 13

Lab Practice: Challenge labs, timed exercises, try harder machines

Week 14

Lab Practice: Full mock exam (5 machines in 24 hours with report)

Week 15

Report Writing: Practice professional report writing, refine templates

Week 16

Final Review: Weak areas, exam strategy, rest and preparation

Free Resources

Proving Grounds

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