README

# NotJeket: A Pentesting Project Overview

## Introduction
NotJeket is a comprehensive pentesting project focusing on the security analysis of multiple virtual machines (VMs), including a diverse range of Windows environments and a Debian 12 VM configured as a router. This document outlines the project's setup, configuration, and execution, emphasizing practical pentesting approaches and tools.

## Project Configuration

### Pre-Planning and VirtualBox Setup
- **Objective**: Ensure VMs can communicate within a private network, isolated from external networks.
- **Implementation**: Utilization of a NAT-Network in VirtualBox, enabling DHCP for automatic IP address assignment.

### Debian 12 VM Router Configuration
- **Network Adapters**: Two adapters configured; a bridged adapter for internet access and a NAT-Network adapter for internal network communication.
- **Network Topology**: Adopted a STAR network topology to route all traffic through the Debian VM, acting as a router.

### Debian Router Setup Steps
1. **Enable IP Forwarding**: Modified `sysctl.conf` to allow IP forwarding.
2. **Network Adapter Identification**: Used `ip addr show` to identify and configure network adapters.
3. **Traffic Masquerading**: Installed `iptables` and added rules to masquerade traffic between adapters.

### Windows VM Settings
- **Configuration**: Enabled network sharing, installed antivirus, and activated various protocols and services to mimic an end-user environment.
- **Software Installation**: Deployed common applications and utilities to replicate a typical user's setup.

## Pentesting VM Configuration
- **Selection**: Chose Parrot OS for the pentesting VM, emphasizing on updating the system before proceeding with pentesting activities.

## Pentesting Phases

### Information Gathering
- **Tool Used**: `nmap` for network scanning and identifying open ports and services on the target VMs.

### Vulnerability Assessment
- **Tools**: MetaSploit and ExploitDB for identifying and exploiting vulnerabilities.
- **Process**: Setting target hosts (`RHOSTS`) and searching for available exploits based on the OS version and services identified.

### Exploit Execution
- **Windows 8.1 VM**: Demonstrated with a proof of concept using the MS15-100 vulnerability.
- **Windows 10 and Windows 11 VMs**: Illustrated different exploit strategies, including browser-based exploits and privilege escalation techniques.

## Conclusion
The project NotJeket provides a deep dive into practical pentesting against a controlled environment of Windows and Debian VMs. It highlights the critical steps for setting up a pentesting lab, conducting information gathering, vulnerability assessment, and executing exploits to understand the security posture of the target systems.