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Information Gathering

Effective information gathering lays the foundation for a successful penetration testing engagement, providing insights into the target application's architecture, network infrastructure, technology stack, and application workflow. Here are key aspects to consider during the information gathering phase:

1. Application Architecture

Understanding the architecture of the application is crucial for identifying potential attack vectors:

  • Two-Tier or Three-Tier Architecture: Determine whether the application operates on a client-server model (two-tier) or includes an intermediary application server (three-tier). This knowledge helps prioritize attack surfaces, such as APIs or direct database access.

2. Network Analysis

Performing network analysis during installation or operation can reveal valuable information:

  • Traffic Observation: Monitor network traffic to identify any sensitive information transmitted in plaintext, such as credentials or proprietary data.

  • Destination IP and Routing: Note destination IP addresses and understand the routing mechanisms to map the data flow within the network. This understanding helps widen the attack surface and identify potential chokepoints or critical infrastructure.

3. Technology Stack

Identifying the technologies and versions used in the application stack is essential for targeting known vulnerabilities:

  • Tools like DetectItEasy: Utilize tools like DetectItEasy to analyze binaries and identify the programming language, frameworks, and libraries used.

  • Vulnerability Assessment: Check if the versions used are vulnerable to any known CVEs (Common Vulnerabilities and Exposures) and prioritize them for further exploitation.

4. Application Workflow

Understanding the application's workflow is key to uncovering unique vulnerabilities and exploitation opportunities:

  • Business Logic Analysis: Gain insights into the application's business logic and unique functionalities to identify potential vulnerabilities or misuse of features.

  • Feature or Function Exploitation: Exploit weaknesses in the application's features or functions by manipulating the workflow or abusing functionality to achieve unauthorized access or privilege escalation.