Skip to main content

Documentation Index

Fetch the complete documentation index at: https://rootea.es/llms.txt

Use this file to discover all available pages before exploring further.

OSCP Roadmap — curated machines

Editorial list of 30 machines ordered by difficulty and vector type, designed to reach the OSCP with the muscle trained. If you own these, the exam won’t surprise you.
The OSCP isn’t passed with theory: it’s passed with hours on machines. This list is complementary to PWK; it doesn’t replace it.

Block 1 — Fundamentals (10 machines, all easy Linux/Windows)

Basic vectors: enumeration, classic buffer overflow, LFI/RFI, SMB.
#MachineOSWhy
1LameLinuxFirst step: enumerate and attack SMB.
2LegacyWindowsMS17-010 without having to fight it.
3DevelWindowsAnonymous FTP + ASPX upload. Classic.
4BeepLinuxMultiple LFI paths, forces enumeration.
5OptimumWindowsHFS RCE + kernel exploit privesc.
6BashedLinuxphpbash + cron abuse. Two gems.
7ShockerLinuxReal Shellshock, not in the lab.
8BlueWindowsEternalBlue to warm up the hand.
9MiraiLinuxDefault credentials + USB forensics.
10GrannyWindowsWebDAV upload + Windows privesc.

Block 2 — Active Directory (10 machines)

The modern OSCP weighs heavily on AD. If this trips you up, you fail.
#MachineOSWhy
11ActiveWindowsGPP + basic Kerberoasting. The intro to AD.
12SaunaWindowsAS-REP Roasting + autologon.
13ForestWindowsFull AD: BloodHound + DCSync.
14ResoluteWindowsDnsAdmins + DLL hijacking.
15MonteverdeWindowsAzure AD Connect, less common vector.
16CascadeWindowsLDAP + credential decryption.
17IntelligenceWindowsDNS dynamic update + delegation.
18BlackfieldWindowsAdvanced Kerberoasting + shadow credentials.
19SearchWindowsExhaustive AD enum, almost like an exam.
20AcuteWindowsPowerShell Web Access + complex AD chain.

Block 3 — Heavy web (5 machines)

The exam’s web points often decide pass or fail.
#MachineOSWhy
21BountyhunterLinuxClassic XXE, well explained.
22KnifeLinuxPHP backdoor RCE, easy but fast.
23SchooledLinuxFull Moodle chain.
24ValidationLinuxSQLi to RCE via INTO OUTFILE.
25BackendtwoLinuxAPI enum + JWT abuse.

Block 4 — Linux privesc (5 machines)

Sudo, SUID, capabilities, kernel.
#MachineOSWhy
26TabbyLinuxTomcat + lxd group.
27PandoraLinuxSNMP enum + multi-step privesc.
28CapLinuxCapabilities, less common vector.
29LateLinuxFlask SSTI + service abuse.
30BackdoorLinuxLFI to RCE + screen abuse.

How to use this roadmap

  1. Don’t skip blocks. Block 2 (AD) assumes you’ve warmed up on basic Linux and Windows.
  2. Time yourself. If a machine takes more than 4h without hints, read the writeup and move on. The goal is patterns, not pride.
  3. Take notes. A solved machine yields 1-2 pages of personal notes; without notes, you’ll review it in 3 weeks and won’t remember.
  4. After each block: re-do a machine from the previous block without hints. If you stumble, repeat it.
This roadmap is opinionated and editorial. If you think a machine is missing or one shouldn’t be there, open a PR against docs/en/roadmap-oscp.mdx.