Gianfranco's Notes

    00 OSCP Master Study Plan

    5 min readUpdated Jul 24, 2026

    Created: 2026-07-24 13:50
    #note

    🎯 OSCP Master Study Plan (Aug - Dec 2026)

    [!important] Exam & Subscription Strategy

    • Subscription Expiry: Early December 2026.
    • Exam Attempt #1: Target Late October / First Week of November (Oct 26 – Nov 1, 2026).
    • Mandatory Cooling-Off Window: Nov 2 – Nov 15, 2026.
    • Exam Attempt #2 (Retake Buffer): Target Late November (Nov 16 – Nov 29, 2026) — Safely before subscription expiry!

    📌 Weekly Study Schedule & Capacity

    • Mon - Thu (1 hr/day max): Theory, module reading, PortSwigger/Tib3rius videos, note taking in Obsidian, command cheat sheet refinement.
    • Friday (Dedicated Deep-Dive Day, 8–10 hrs): Practical machine exploitation, PEN-200 Challenge Labs, AD domain compromise, full mock exams.
    • Total Capacity: ~12–14 hours per week.

    📊 16-Week Weekly Schedule Breakdown Table

    WeekDate RangeLinear CycleLinear MilestonePrimary Focus & Deliverables
    W1Jul 27 – Aug 2Cycle 1Milestone 1Vault Setup & PEN-200 Modules 1–5 (CLI, Bash, Nmap, Netcat)
    W2Aug 3 – Aug 9Cycle 2Milestone 1PEN-200 Modules 6–10 (Recon & Burp Suite) + Tib3rius Linux PrivEsc (ClamAV)
    W3Aug 10 – Aug 16Cycle 3Milestone 1PEN-200 Modules 11–15 (Web SQLi/LFI, Exploit Fix) + TCM AD (Nibbles, Helpdesk, Kevin)
    W4Aug 17 – Aug 23Cycle 4Milestone 1Phase 1 Polish & Standalone Warmup (HTB Active AD)
    W5Aug 24 – Aug 30Cycle 5Milestone 2PEN-200 Modules 16–24 & Tib3rius Windows PrivEsc (Medtech Lab M1)
    W6Aug 31 – Sep 6Cycle 6Milestone 2PortSwigger Web Academy & Medtech Lab M2 / DC Compromise
    W7Sep 7 – Sep 13Cycle 7Milestone 2PEN-200 Challenge Lab 2: Relia (M1 & M2 Domain Pwning)
    W8Sep 14 – Sep 20Cycle 8Milestone 2AD Kerberoasting & Relia DC + PG Practice (Hutch, Heist)
    W9Sep 21 – Sep 27Cycle 9Milestone 3Ligolo-ng Pivoting & Tunneling Masterclass (HTB Forest, Sauna)
    W10Sep 28 – Oct 4Cycle 10Milestone 3Skylark Enterprise Lab (Part 1 - Dual-Homed Pivoting & PG Hotline, Syringe)
    W11Oct 5 – Oct 11Cycle 11Milestone 3Skylark Enterprise Lab (Part 2 - Domain Trust Pwning & PG Hekate, Pebble)
    W12Oct 12 – Oct 18Cycle 12Milestone 3TJnull Medium Standalones (Craft, PyScript, Sentinel, Internal)
    W13Oct 19 – Oct 25Cycle 13Milestone 4OSCP-A 24-hr Mock Exam Simulation & Report Writing Practice
    W14Oct 26 – Nov 1Cycle 14Milestone 4🎯 EXAM ATTEMPT #1 (Sit Official OSCP Exam + 24h Report)
    W15Nov 2 – Nov 15Cycle 15Milestone 4Cooling-Off Window / Weak Vector Refinement & OSCP-B Mock Exam
    W16Nov 16 – Nov 29Cycle 16Milestone 4🛡️ EXAM ATTEMPT #2 (Backup Retake Window before sub expiry)

    Phase 1: Foundations, Web & AD Fundamentals (August 2026)

    • Cycle 1 (Jul 27 – Aug 2): PEN-200 Modules 1–5 (Orientation, Linux CLI, Bash Scripting, Netcat, Nmap basics) + Obsidian Vault Setup.
    • Cycle 2 (Aug 2 – Aug 9): PEN-200 Modules 6–10 (Recon, Port Scanning, Web App Intro, Burp Suite) + Tib3rius Linux PrivEsc.
    • Cycle 3 (Aug 9 – Aug 16): PEN-200 Modules 11–15 (Web Attacks: SQLi, LFI/RFI, Cmd Injection; Exploit Fixing; AV Evasion) + TCM PEH AD Section.
    • Cycle 4 (Aug 17 – Aug 23): Standalone Warmup Machines (ClamAV, Nibbles, Helpdesk, Kevin, Active).
    • Key Resources:

    Phase 2: PEN-200 Course Completion & Challenge Labs (September 2026)

    Phase 3: Advanced Enterprise Labs & Pivoting (October 2026)

    Phase 4: Mock Exams & Exam Attempts (November - Early December 2026)

    • Cycle 13 (Oct 18 – Oct 25): 24-hr Simulation — Official OSCP-A Mock Exam.
    • Cycle 14 (Oct 26 – Nov 1): 🎯 EXAM ATTEMPT #1
    • Cycle 15 (Nov 1 – Nov 15): Weak point refinement, PG Practice hard standalones, OSCP-B Mock Exam.
    • Cycle 16 (Nov 16 – Nov 29): 🛡️ EXAM ATTEMPT #2 (Backup retake window before sub expiry!)
    • Key Resources:

    Tags

    #oscp #study_plan #certification #penetration_testing #active_directory #cybersecurity

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