Cryptographic Attack Mitigation Playbook

December 16, 20234 min read

Playbook Objectives

  • To enhance the understanding and response capability of the IT security team in the event of a cryptographic attack.
  • To evaluate the effectiveness of existing encryption protocols and identify potential weaknesses.
  • To train and prepare the incident response team for rapid detection, containment, isolation, and remediation of a cryptographic attack.
  • To validate and improve the current cryptographic attack response and recovery plan.

Difficulty Level

  • Advanced: Participants should have proficient knowledge of encryption algorithms, public-key infrastructure (PKI), and cryptographic attack vectors.

Scenario Company Background:

  • Company Name: Quantum Secure Inc.
  • Industry: Financial Services
  • Location: Metropolis, USA
  • Size: 500+ employees
  • Network Structure: A central data center, multiple branch offices connected via VPN, cloud services for customer data storage, and a dedicated R&D department.
  • Systems: Firewall, IDS/IPS, SIEM, PKI server, custom encryption software for sensitive customer transactions.
  1. Story: In the wake of recent breaches in several high-profile financial institutions, Quantum Secure Inc., known for its robust security measures and financial services technology, realizes the need to reassess and fortify its cryptographic defenses.
  2. The board of directors has mandated a comprehensive audit and stress-test of the company’s cryptographic infrastructure. This is not just a routine check but a reaction to an anonymous tip that a group of sophisticated cybercriminals is targeting Quantum Secure’s custom encryption software.
  3. The R&D department’s team lead, Dr. Natasha Cipher, alongside the CISO, Mr. Alan Turing, decides to initiate a Cyber Range exercise focused on Cryptographic Attack Mitigation. The exercise is designed to simulate an adversary that is attempting to exploit vulnerabilities in Quantum Secure’s encryption protocols.
  4. By running this intensive lab exercise, the team aims to locate and secure potential weak points, adapt incident response strategies for cryptographic attacks, and ensure the company’s network and customer data remain impenetrable.


  • Cryptography
  • Incident Response
  • Threat Simulation

Exercise Attack Steps

  1. Initiate a reconnaissance phase where the simulated adversaries map out Quantum Secure’s network topology, identifying the encryption protocols in use and the location of the PKI server.
  2. Engage a vulnerability scanning process against the company’s encryption infrastructure, searching for outdated protocols like SSL 2.0 or weak cipher suites that could be susceptible to attacks like Heartbleed or POODLE.
  3. Follow the vulnerability scanning with exploitation attempts, such as crafting a BEAST (Browser Exploit Against SSL/TLS) attack against their online services to test the mitigation techniques of their SSL/TLS implementations.
  4. Simulate an insider threat capable of stealing a set of private keys from the PKI server, prompting the need for key revocation and reissuance procedures.
  5. Fabricate an attack designed to intercept and decrypt data in transit, employing a man-in-the-middle (MITM) strategy to assess the robustness of end-to-end encryption mechanisms.
  6. Conduct a brute-force attack against the R&D department’s custom encryption algorithm to evaluate its resistance to computational attacks and to test rate-limiting defenses.
  7. Test the strength of Quantum Secure’s password hashing methods by simulating a password-cracking attempt, using techniques like rainbow tables or dictionary attacks.
  8. Simulate a supply chain attack where threat actors try to introduce a backdoor in a cryptographic library that Quantum Secure relies on. This step assesses the integrity of third-party code and the effectiveness of supply chain security measures.
  9. Execute a key exchange interception attempt during a simulated new device enrollment to test the security of session initiation protocols.
  10. Wrap up the exercise with a post-attack phase, analyzing log files, and SIEM alerts to determine the levels of detection, creating forensic reports, and refining incident response actions.