OSCP+ .111 Standalone Machine (10 Points)
Target Infrastructure:
Machine IP: 192.168.xx.111 running:
- 21 (Microsoft ftpd – FTP )
- 80 (Microsoft IIS httpd 10.0 – Offsec Employee Portal)
- 3389 (Microsoft Terminal Services – RDP)
- 5985 (Microsoft HTTPAPI httpd 2.0 – WinRM)
• 10 Points Set: Contains the complete sequence to secure both user and Administrator/SYSTEM flags for maximum points on this specific target.
• Clear Exploitation Path: Easy-to-copy-and-paste commands fully documented for immediate terminal execution.
• Images Included: Visual confirmation for every critical step of the exploitation process.
• Post-Purchase Support: Direct communication channels remain open for any technical clarifications during your prep.
OSCP+ .111 Standalone Exploitation Methodology
The OSCP+ .111 standalone exploitation methodology focuses on systematically enumerating a Windows target, identifying the most promising attack vectors, and progressing from initial access to Administrator-level privileges. For OSCP+ candidates, this machine provides practical experience with multiple exposed Windows services and a complete standalone exploitation workflow.
Initial enumeration of the .111 target reveals several important services. FTP is exposed on port 21, while port 80 hosts an OffSec Employee Portal running on Microsoft IIS 10.0. The system also exposes Remote Desktop Protocol (RDP) on port 3389 and WinRM on port 5985, creating multiple potential paths for credential discovery, authentication, remote access, and post-exploitation.
The objective is to determine how these services interact rather than testing vulnerabilities randomly. FTP content, the employee portal, accessible files, credentials, application functionality, and Windows services should be examined carefully to identify the intended path toward the initial foothold.
Initial Access and Privilege Escalation
The OSCP+ .111 exploitation methodology begins with comprehensive service enumeration. FTP should be checked for anonymous access, readable files, configuration information, credentials, and other data that could provide additional context about the target. The IIS-hosted employee portal should then be analyzed through endpoint discovery, HTTP request inspection, authentication testing, and application fingerprinting.
Any credentials or sensitive information discovered during enumeration should also be tested against relevant remote management services where appropriate. With RDP and WinRM available, valid Windows credentials may provide an alternative or direct route into the target.
A structured attack path for the .111 standalone machine follows this progression:
Port & Service Enumeration → FTP Analysis → IIS Web Enumeration → Credential & Vulnerability Discovery → Initial Foothold → Windows Local Enumeration → Privilege Escalation → Administrator Access
After obtaining the initial shell, attention shifts to Windows privilege escalation. Local enumeration should cover the current user’s privileges, running services, scheduled tasks, installed applications, stored credentials, filesystem permissions, service configurations, and other potential escalation vectors.
Target Profile and OSCP+ Exam Preparation
OSCP Candidates: Practice completing an end-to-end standalone Windows attack path covering both initial access and local privilege escalation.
Focused Enumeration: Prioritize evidence discovered through FTP, IIS, RDP, and WinRM instead of spending valuable lab time testing unrelated attack paths.
Repeatable Commands: Follow organized enumeration and exploitation commands that can be reproduced consistently during OSCP lab practice.
Complete Attack Documentation: Record important commands, screenshots, discovered vulnerabilities, proof files, and privilege escalation steps throughout the process to build stronger OSCP-style reporting habits.
The OSCP+ .111 standalone exploitation methodology reinforces one of the most important skills in PEN-200 preparation: connecting information discovered across multiple services. Instead of treating FTP, the OffSec Employee Portal, RDP, and WinRM as isolated attack surfaces, candidates should use each discovery to guide the next stage of enumeration until a reliable path from initial access to Administrator privileges is established.