Man-in-the-Middle (MITM) Attack Simulation Playbook

December 17, 20233 min read

Playbook Objectives:

  • To enhance the company’s defensive capabilities towards MITM attacks.
  • To detect any potential network weaknesses that a cybercriminal might exploit for a MITM attack.
  • To understand and evaluate the existing security measures’ effectiveness and possibly improve them.
  • To improve the team’s response to potential MITM attacks in real situations.
  • To educate the team on how a MITM attack could infiltrate the company’s network and how to prevent it.

Difficulty level:

  • Intermediate


  • TechSolution Corp, a top-tier cybersecurity software company located in Silicon Valley, is planning an exercise to simulate a Man-in-the-Middle attack. The company is actively developing advanced security technologies for corporate networks, making it a target for cybercriminals, corporate spies and black hat hackers wanting to expose potential flaws or steal proprietary information.
  • The CISO (Chief Information Security Officer) “John Doe”, understands the risks and has planned a MITM attack simulation to expose any network weaknesses and beef up the company’s defenses. This simulation will also serve as a learning experience for the entire team to understand how cybercriminals could infiltrate the network.
  • TechSolution Corp has a massive network containing various classified and sensitive data. It primarily uses an intranet system for internal communication, along with a connected VPN for off-site employees. On-site, they have a Wi-Fi network connected to this intranet.
  • The CISO and his team have identified these as potential vulnerabilities for a MITM attack and will include them in the simulation. The primary objective for this exercise is to impact the company’s continuous efforts towards a more robust and impervious network, ensuring overall business continuity.


  • Cybersecurity – Man in the Middle Attack

Exercise Attack Steps:

  • Reconnaissance: Identify key systems, key personnel, network architecture and the security measures in place at TechSolution Corp.
  • Weaponization: Set up interceptor device or software capable of intercepting and altering network traffic between devices.
  • Delivery: Deploy the MITM attack setup within the company’s network, focusing either on the intranet or the Wi-Fi network for maximum disruption.
  • Exploitation: Use the interceptor to infiltrate the traffic and attempt to access classified and sensitive data being transmitted.
  • Installation: Attempt to maintain access within the system by installing malicious software or exploit the system’s network for as long as possible before detection.
  • Control: Proceed to manipulate or control the information flow if the attack remains undetected. This step involves redirecting, altering or deleting packets of information as they are transmitted.
Post the exercise, the cybersecurity team will analyze the shortcomings in the current defenses and create a more robust strategy using this knowledge. The teams’ understanding of the nature and mechanics of MITM attacks will also be significantly enhanced, improving the overall cybersecurity posture of TechSolution Corp.