Broken Cryptography | CQR (2024)

Broken cryptography refers to situations where encryption algorithms or other cryptographic mechanisms are implemented incorrectly or used in a way that leaves them vulnerable to attacks. This can happen due to various reasons such as flawed design, implementation errors, incorrect usage, or weak cryptographic keys.

When cryptography is broken, attackers can potentially access confidential information, modify data, or impersonate legitimate users, causing serious security risks. It is essential to use secure and properly implemented cryptography to protect sensitive data and maintain the integrity of computer systems and networks.

• Web Vulnerabilities
• Pentesting process
• Reportings
• Compliance
• Protocols

Example of vulnerable code on different programming languages:

• in Python:

Password cracking:

One of the most common ways to exploit broken cryptography is to crack passwords that have been hashed using insecure algorithms such as MD5 or SHA-1. Attackers can use precomputed hash tables or brute force methods to guess the plaintext password corresponding to the hash. Once they have the plaintext password, they can use it to log into the victim’s account and carry out further attacks.

Man-in-the-middle attacks:

Another way to exploit broken cryptography is to perform man-in-the-middle (MITM) attacks on encrypted communication channels. For example, if the SSL/TLS certificate used by a website is generated using weak cryptographic keys, an attacker can use a technique called “SSL stripping” to downgrade the connection to an insecure HTTP channel and intercept sensitive information such as login credentials or credit card numbers.

Cryptographic side-channel attacks:

Broken cryptography can also be exploited through side-channel attacks that target the implementation of the cryptographic algorithm rather than the algorithm itself. For example, attackers can use techniques such as timing attacks, power analysis, or electromagnetic analysis to extract sensitive information such as encryption keys or plaintext from a device’s memory or processing units. These attacks can be particularly effective against embedded systems or devices with limited computational resources.

Data tampering:

Finally, broken cryptography can be exploited to modify or tamper with encrypted data in transit or at rest. For example, if the encryption key used to protect a database is compromised, an attacker can modify or delete sensitive data, or insert malicious code into the database. This can lead to data breaches, financial losses, and reputational damage for the victim.

Exploiting weak encryption keys:

If the cryptographic keys used to protect sensitive data are weak or predictable, attackers can use techniques such as brute force attacks or rainbow tables to crack the encryption and gain access to the plaintext. Once they have the plaintext, they can use it to escalate their privileges or access other sensitive resources on the system.

Tampering with encryption-related configuration files:

If an attacker can gain access to configuration files or registry keys related to cryptography, they can modify them to disable or weaken encryption, or redirect traffic to a malicious server. For example, an attacker could modify the “hosts” file on a victim’s computer to redirect traffic from a legitimate SSL/TLS certificate to a fake one they control, allowing them to carry out a man-in-the-middle attack and intercept sensitive data.

Exploiting insecure key storage:

If cryptographic keys are stored in an insecure manner, such as in plaintext files or in system memory, attackers can steal them and use them to escalate their privileges or access other sensitive resources on the system. For example, if an application stores encryption keys in a configuration file that is accessible to all users, an attacker with low-level access to the system could steal the keys and use them to decrypt sensitive data.

Abusing cryptographic protocols:

If cryptographic protocols are implemented incorrectly or used in a way that leaves them vulnerable to attacks, attackers can abuse them to escalate their privileges or access sensitive data. For example, an attacker could use a padding oracle attack to decrypt encrypted data or forge digital signatures, or use a side-channel attack to extract encryption keys from a victim’s system memory.

Methodology:

1. Identify cryptographic mechanisms in use: The first step is to identify the cryptographic mechanisms that are used to protect data or communications, such as encryption algorithms, key management procedures, and digital signature protocols.

2. Identify potential vulnerabilities: Once the cryptographic mechanisms are identified, the next step is to identify potential vulnerabilities or weaknesses in their implementation or usage. This can include using weak encryption algorithms, using weak or predictable keys, storing keys or other sensitive information in an insecure manner, or failing to protect against side-channel attacks.

3. Test the cryptographic mechanisms: Once potential vulnerabilities have been identified, the next step is to test the cryptographic mechanisms to see if they can be exploited to compromise sensitive data or communications. This can involve using techniques such as brute-force attacks, cryptographic analysis, reverse engineering, or penetration testing.

4. Analyze results: The results of the testing should be analyzed to determine the effectiveness of the cryptographic mechanisms in protecting sensitive data or communications. If weaknesses are identified, recommendations for remediation should be provided.

5. Document findings: The findings of the testing should be documented in a clear and concise manner, along with any recommended remediation steps. This documentation can be used to guide future testing and to ensure that any identified weaknesses are addressed in a timely and effective manner.

6. Retest: It is important to periodically retest the cryptographic mechanisms to ensure that any identified weaknesses have been addressed and that the mechanisms remain effective in protecting sensitive data or communications.

Checklist:

1. Identify cryptographic mechanisms in use, such as encryption algorithms, key management procedures, and digital signature protocols.

2. Check that the cryptographic mechanisms are implemented according to best practices and industry standards.

3. Check the strength of cryptographic keys, passwords, and other secrets used in the system.

4. Check for proper key management practices, including key rotation and secure key storage.

5. Check that the cryptographic mechanisms are properly integrated into the system, including any application programming interfaces (APIs) and libraries.

6. Check that the cryptographic mechanisms are resistant to common attacks, such as brute-force attacks, known plaintext attacks, chosen plaintext attacks, and man-in-the-middle attacks.

7. Check that the cryptographic mechanisms are properly configured, including using the correct encryption mode, padding scheme, and key size.

8. Check that the cryptographic mechanisms are properly used throughout the system, including protecting sensitive data in transit and at rest.

9. Check for implementation flaws, such as buffer overflows or other memory management errors, that may be exploited to bypass or weaken cryptographic protections.

10. Check for side-channel attacks that may allow an attacker to extract sensitive information through analysis of system behavior or electromagnetic emissions.

11. Check that the system has proper logging and monitoring in place to detect and respond to any attempts to exploit weaknesses in the cryptographic mechanisms.

12. Check that the system has proper access controls in place to limit the exposure of sensitive data to unauthorized users.

13. Document findings and recommendations for remediation, including any necessary changes to the cryptographic mechanisms or system configuration.

Manual Tools:

• OpenSSL: A widely-used open source cryptography library that can be used for manual testing and exploitation of cryptographic vulnerabilities. OpenSSL provides a command-line interface for testing cryptographic mechanisms.

• John the Ripper: A password cracking tool that can be used to test the strength of cryptographic keys, passwords, and other secrets used in the system. John the Ripper supports a wide range of encryption algorithms and key formats.

• Burp Suite: A popular web application security testing tool that includes a range of features for testing cryptographic mechanisms, such as scanning for weak encryption algorithms and identifying cryptographic implementation flaws.

• Wireshark: A network protocol analyzer that can be used to capture and analyze network traffic, including encrypted traffic. Wireshark includes features for decrypting SSL/TLS traffic and analyzing cryptographic exchanges.

• Cryptool: A free, open-source tool for testing and analyzing cryptographic mechanisms, including encryption algorithms, digital signature protocols, and key management procedures.

• Kali Linux: A popular Linux distribution for penetration testing and security auditing that includes a wide range of tools for testing cryptographic mechanisms and exploiting cryptographic vulnerabilities.

• Aircrack-ng: A wireless network security testing tool that includes features for cracking Wi-Fi encryption and analyzing wireless network traffic.

• Hydra: A password cracking tool that can be used to test the strength of passwords and other secrets used in the system. Hydra supports a wide range of authentication protocols and encryption algorithms.

• Metasploit: A widely-used framework for developing and executing exploit code against vulnerable systems. Metasploit includes modules for exploiting cryptographic vulnerabilities and testing cryptographic mechanisms.

• SQLMap: A tool for testing and exploiting SQL injection vulnerabilities in web applications. SQLMap includes features for testing cryptographic implementation flaws and bypassing encryption mechanisms.

Automated Tools:

• Nmap: A network scanning tool that includes features for identifying open ports, services, and vulnerabilities. Nmap can be used to identify systems that are vulnerable to cryptographic attacks.

• Nessus: A vulnerability scanning tool that includes a wide range of checks for identifying security vulnerabilities, including cryptographic implementation flaws and weak encryption algorithms.

• Nikto: A web server vulnerability scanner that includes checks for identifying insecure cryptographic mechanisms and implementation flaws.

• OpenVAS: An open source vulnerability scanning tool that includes a wide range of checks for identifying security vulnerabilities, including cryptographic implementation flaws and weak encryption algorithms.

• OWASP ZAP: A web application security testing tool that includes features for identifying insecure cryptographic mechanisms and implementation flaws.

• SSLyze: A tool for testing and analyzing SSL/TLS implementations. SSLyze includes features for identifying insecure cryptographic configurations and implementation flaws.

• THC-Hydra: A parallelized login cracker that can be used to test the strength of passwords and other secrets used in the system. THC-Hydra supports a wide range of authentication protocols and encryption algorithms.

• W3af: A web application security testing tool that includes features for identifying insecure cryptographic mechanisms and implementation flaws.

• GnuPG: A free, open-source implementation of the OpenPGP standard for encrypting and signing data. GnuPG includes features for testing and analyzing cryptographic mechanisms, as well as for generating and managing keys.

• Hashcat: A password cracking tool that can be used to test the strength of passwords and other secrets used in the system. Hashcat supports a wide range of encryption algorithms and key formats.

•CWE-327: Use of a Broken or Risky Cryptographic Algorithm – this weakness involves the use of a cryptographic algorithm that has known vulnerabilities or weaknesses.

•CWE-310: Cryptographic Issues – this weakness encompasses a broad range of cryptographic vulnerabilities, including key management errors, weak random number generation, and insecure key storage.

•CWE-338: Use of Cryptographically Weak Pseudo-Random Number Generators (PRNG) – this weakness involves the use of predictable or weak pseudo-random number generators, which can make cryptographic systems vulnerable to attacks.

•CWE-347: Improper Verification of Cryptographic Signature – this weakness involves failing to properly verify cryptographic signatures, which can allow attackers to modify data without detection.

•CWE-350: Reliance on Reverse Engineering of Cryptographic Algorithms – this weakness involves relying on the secrecy of a cryptographic algorithm rather than its mathematical strength.

•CWE-352: Cross-Site Request Forgery (CSRF) – this weakness involves the manipulation of a cryptographic token used to prevent CSRF attacks, resulting in the bypass of the token’s protection.

•CWE-327: Predictable IV – this weakness involves using a predictable initialization vector (IV) in a cryptographic system, which can allow attackers to decrypt data or manipulate the encryption.

•CWE-326: Inadequate Encryption Strength – this weakness involves using cryptographic algorithms with inadequate key lengths or other weaknesses, which can make the encryption vulnerable to attack.

•CWE-328: Reversible One-Way Hash – this weakness involves the use of a one-way hash function that can be reversed, allowing attackers to discover the original plaintext.

•CWE-330: Use of Insufficiently Random Values – this weakness involves the use of insufficiently random values, such as weak passwords or predictable session IDs, which can make cryptographic systems vulnerable to attack.

•CVE-2023-24025 – CRYSTALS-DILITHIUM (in Post-Quantum Cryptography Selected Algorithms 2022) in PQClean d03da30 may allow universal forgeries of digital signatures via a template side-channel attack because of intermediate data leakage of one vector.

•CVE-2023-23931 – cryptography is a package designed to expose cryptographic primitives and recipes to Python developers. In affected versions `Cipher.update_into` would accept Python objects which implement the buffer protocol, but provide only immutable buffers. This would allow immutable objects (such as `bytes`) to be mutated, thus violating fundamental rules of Python and resulting in corrupted output. This now correctly raises an exception. This issue has been present since `update_into` was originally introduced in cryptography 1.8.

•CVE-2023-23695 – Dell Secure Connect Gateway (SCG) version 5.14.00.12 contains a broken cryptographic algorithm vulnerability. A remote unauthenticated attacker could potentially exploit this vulnerability by performing MitM attacks and let attackers obtain sensitive information.

•CVE-2023-22471 – Deck is a kanban style organization tool aimed at personal planning and project organization for teams integrated with Nextcloud. Broken access control allows a user to delete attachments of other users. There are currently no known workarounds. It is recommended that the Nextcloud Deck app is upgraded to 1.6.5 or 1.7.3 or 1.8.2.

•CVE-2022-46834 – Use of a Broken or Risky Cryptographic Algorithm in SICK RFU65x firmware version < v2.21 allows a low-privileged remote attacker to decrypt the encrypted data if the user requested weak cipher suites to be used for encryption via the SSH interface. The patch and installation procedure for the firmware update is available from the responsible SICK customer contact person.

•CVE-2022-46833 – Use of a Broken or Risky Cryptographic Algorithm in SICK RFU63x firmware version < v2.21 allows a low-privileged remote attacker to decrypt the encrypted data if the user requested weak cipher suites to be used for encryption via the SSH interface. The patch and installation procedure for the firmware update is available from the responsible SICK customer contact person.

•CVE-2022-46832 – Use of a Broken or Risky Cryptographic Algorithm in SICK RFU62x firmware version < 2.21 allows a low-privileged remote attacker to decrypt the encrypted data if the user requested weak cipher suites to be used for encryption via the SSH interface. The patch and installation procedure for the firmware update is available from the responsible SICK customer contact person.

•CVE-2022-45475 – Tiny File Manager version 2.4.8 allows an unauthenticated remote attacker to access the application’s internal files. This is possible because the application is vulnerable to broken access control.

•CVE-2022-45369 – Auth. (subscriber+) Broken Access Control vulnerability in Plugin for Google Reviews plugin <= 2.2.2 on WordPress.

•CVE-2022-45353 – Broken Access Control in Betheme theme <= 26.6.1 on WordPress.

• Heartbleed: This is a vulnerability in OpenSSL that allows an attacker to read sensitive information, such as private keys and passwords, from the memory of a vulnerable server.

• POODLE: This is a vulnerability in SSL 3.0 that allows an attacker to decrypt data transmitted between a client and server.

• BEAST: This is a vulnerability in SSL/TLS that allows an attacker to intercept and decrypt data transmitted between a client and server.

• DROWN: This is a vulnerability in SSL/TLS that allows an attacker to decrypt data transmitted between a client and server using a vulnerable implementation of SSLv2.

• FREAK: This is a vulnerability in SSL/TLS that allows an attacker to force a client to use weak encryption, making it easier to decrypt the transmitted data.

• Logjam: This is a vulnerability in the Diffie-Hellman key exchange algorithm that allows an attacker to decrypt data transmitted between a client and server.

• ROBOT: This is a vulnerability in SSL/TLS that allows an attacker to decrypt data transmitted between a client and server by exploiting a flaw in the RSA encryption process.

• Padding Oracle Attack: This is an attack that exploits vulnerabilities in the padding used in block cipher encryption modes, allowing an attacker to decrypt data transmitted between a client and server.

• Sweet32: This is an attack that exploits vulnerabilities in block ciphers with a block size of 64 bits, allowing an attacker to decrypt data transmitted between a client and server.

• Lucky13: This is an attack that exploits vulnerabilities in the implementation of the TLS protocol, allowing an attacker to decrypt data transmitted between a client and server.

Use intentionally vulnerable applications: There are many intentionally vulnerable applications available online, such as DVWA and WebGoat, that allow you to practice testing for various security vulnerabilities, including broken cryptography.

Participate in CTFs: Capture the Flag (CTF) competitions often include challenges related to cryptography and encryption, providing a great opportunity to practice testing for broken cryptography in a competitive environment.

Conduct penetration testing on your own systems: If you are responsible for securing a system or network, you can conduct penetration testing on your own systems to identify potential vulnerabilities related to broken cryptography.

Attend training and workshops: Many security training courses and workshops include hands-on exercises and labs that allow you to practice testing for broken cryptography in a safe and controlled environment.

Use vulnerability scanning tools: There are many automated vulnerability scanning tools available, such as Nessus and OpenVAS, that can help identify potential vulnerabilities related to broken cryptography.

Read and analyze publicly disclosed vulnerabilities: Keeping up to date with publicly disclosed vulnerabilities related to broken cryptography can help you understand the types of vulnerabilities that exist and how they are exploited.

Join online communities and forums: Joining online communities and forums focused on security testing can provide opportunities to learn from others and ask for feedback on your own testing efforts.

Cryptography I and Cryptography II courses on Coursera: These courses, taught by Dan Boneh of Stanford University, provide a comprehensive introduction to cryptography, including an overview of common attacks and vulnerabilities.

The Handbook of Applied Cryptography: This book, by Alfred J. Menezes, Paul C. van Oorschot, and Scott A. Vanstone, provides a detailed introduction to the field of cryptography, including an overview of common attacks and vulnerabilities.

Cryptography Engineering: Design Principles and Practical Applications: This book, by Niels Ferguson, Bruce Schneier, and Tadayoshi Kohno, provides an overview of the practical implementation of cryptography, including an overview of common attacks and vulnerabilities.

The Cryptopals Crypto Challenges: This is a set of challenges designed to help people learn and practice cryptography skills, including identifying and exploiting vulnerabilities.

The OWASP Top 10: The OWASP Top 10 is a list of the most common vulnerabilities in web applications, including those related to cryptography. Studying this list can help you understand common attack vectors and how to test for them.

Vulnerability Disclosure Programs: Reviewing vulnerability disclosure programs from different companies and organizations can provide insights into the common cryptographic vulnerabilities in software and how they are addressed.

Security Conferences and Workshops: Attending security conferences and workshops can help you stay up to date on the latest research and developments in the field of cryptography and learn from experts in the field.

The Code Book: The Science of Secrecy from Ancient Egypt to Quantum Cryptography by Simon Singh: This book provides an engaging history of cryptography, including an overview of various techniques and their vulnerabilities.

Cryptography Engineering: Design Principles and Practical Applications by Niels Ferguson, Bruce Schneier, and Tadayoshi Kohno: This book provides an overview of the practical implementation of cryptography, including an overview of common attacks and vulnerabilities.

Applied Cryptography: Protocols, Algorithms, and Source Code in C by Bruce Schneier: This classic book provides a comprehensive introduction to cryptography, including an overview of common attacks and vulnerabilities.

Handbook of Applied Cryptography by Alfred J. Menezes, Paul C. van Oorschot, and Scott A. Vanstone: This book provides a detailed introduction to the field of cryptography, including an overview of common attacks and vulnerabilities.

Cryptography for Developers by Tom St. Denis: This book provides a practical guide to implementing cryptography, including an overview of common vulnerabilities and how to avoid them.

Bulletproof SSL and TLS: Understanding and Deploying SSL/TLS and PKI to Secure Servers and Web Applications by Ivan Ristic: This book provides a practical guide to implementing secure SSL/TLS connections, including an overview of common vulnerabilities and how to avoid them.

The Art of Deception: Controlling the Human Element of Security by Kevin Mitnick and William L. Simon: While not focused specifically on cryptography, this book provides an overview of social engineering attacks that can be used to exploit vulnerabilities in cryptographic systems.

Serious Cryptography: A Practical Introduction to Modern Encryption by Jean-Philippe Aumasson: This book provides a practical guide to modern cryptography, including an overview of common vulnerabilities and how to avoid them.

Hacking Exposed 7: Network Security Secrets and Solutions by Stuart McClure, Joel Scambray, and George Kurtz: While not focused specifically on cryptography, this book provides an overview of common network security vulnerabilities, including those related to cryptography.

Practical Cryptography for Developers by Svetlin Nakov and Christos Monogios: This book provides a practical guide to implementing cryptography in software applications, including an overview of common vulnerabilities and how to avoid them.

• Padding oracle attack payloads: These payloads exploit a vulnerability in which an attacker can deduce information about a plaintext message by observing the padding used in an encrypted message. Example payloads may include manipulated padding blocks to reveal plaintext data.

• Chosen ciphertext attack payloads: These payloads exploit a vulnerability in which an attacker can obtain plaintext data by providing carefully crafted ciphertext inputs to a decryption function. Example payloads may include deliberately crafted ciphertexts that cause decryption functions to reveal plaintext data.

• Key reuse attack payloads: These payloads exploit a vulnerability in which a cryptographic key is reused across multiple messages, allowing an attacker to deduce the key and decrypt all messages encrypted with that key. Example payloads may include deliberately crafted messages designed to expose a reused key.

• Collision attack payloads: These payloads exploit a vulnerability in which two different plaintext messages are mapped to the same cryptographic hash value, allowing an attacker to create a false message with the same hash value as a legitimate message. Example payloads may include messages designed to produce collisions in commonly used hash functions.

• Man-in-the-middle attack payloads: These payloads exploit a vulnerability in which an attacker intercepts communications between two parties and can manipulate or eavesdrop on the messages being sent. Example payloads may include crafted messages designed to fool both parties into believing they are communicating with each other when they are really communicating with the attacker.

1. Stay up-to-date on security best practices: Follow security blogs, attend security conferences, and stay informed about the latest security best practices to ensure that you are using the latest and most secure cryptographic protocols and implementations.

2. Use strong encryption algorithms: Use encryption algorithms that are known to be strong and secure, such as AES or RSA.

3. Implement proper key management: Proper key management is crucial to ensuring the security of cryptographic systems. Use strong and unique keys, and rotate them regularly to prevent reuse.

4. Use proper key exchange protocols: When exchanging cryptographic keys, use protocols that are known to be secure, such as Diffie-Hellman key exchange or the Elliptic Curve Diffie-Hellman key exchange.

5. Use secure random number generation: Cryptographic systems often rely on the generation of random numbers. Make sure that your system uses a secure random number generator to prevent attackers from predicting the values.

6. Perform regular vulnerability assessments: Regular vulnerability assessments can help identify weaknesses in your cryptographic systems before they can be exploited by attackers.

7. Implement proper access controls: Limit access to cryptographic systems to only those who need it, and use strong authentication and authorization mechanisms to prevent unauthorized access.

8. Stay vigilant: Monitor your systems for signs of unauthorized access or other suspicious activity, and respond quickly to any security incidents.

1. Patch and update: Keep your software and systems up-to-date with the latest security patches and updates. This can help address known vulnerabilities in cryptographic protocols and implementations.

2. Implement secure key management: Proper key management is essential to ensuring the security of cryptographic systems. Implement secure key management practices, such as using strong and unique keys, rotating keys regularly, and limiting access to keys.

3. Use strong cryptographic algorithms: Use cryptographic algorithms that are known to be strong and secure, and avoid using deprecated or weak algorithms.

4. Implement proper key exchange protocols: When exchanging cryptographic keys, use protocols that are known to be secure, such as Diffie-Hellman key exchange or the Elliptic Curve Diffie-Hellman key exchange.

5. Use secure random number generation: Cryptographic systems often rely on the generation of random numbers. Use a secure random number generator to ensure that keys and other cryptographic data are generated with sufficient entropy.

6. Implement proper access controls: Limit access to cryptographic systems to only those who need it, and use strong authentication and authorization mechanisms to prevent unauthorized access.

7. Implement monitoring and logging: Implement monitoring and logging capabilities to detect and respond to security incidents related to broken cryptography vulnerabilities.

8. Perform regular vulnerability assessments: Regular vulnerability assessments can help identify weaknesses in your cryptographic systems before they can be exploited by attackers.

Cryptography is an essential part of modern information security. It provides a means to protect sensitive data and communications from unauthorized access or modification. However, broken cryptography can pose a significant risk to the security of information systems, as it can allow attackers to bypass or circumvent the cryptographic protections in place.

To prevent and mitigate broken cryptography vulnerabilities, it is important to follow security best practices such as staying up-to-date on security standards, using strong encryption algorithms, implementing proper key management, and performing regular vulnerability assessments. By staying vigilant and implementing these best practices, organizations can help protect their systems against broken cryptography vulnerabilities and ensure the security and privacy of their sensitive information.