Maintaining IT security measures with penetration testing

Penetration tests (Pentests) are attempts to assess the security of IT infrastructure by controlled and secure exploitation of vulnerabilities. Weaknesses may exist in operating systems, services, applications, misconfigurations, or risky end-user behaviours. Such validation proves useful in evaluating the effectiveness of defensive mechanisms and ensuring adherence to security policies by end-users. Pentests are commonly conducted using manual or automated technologies to systematically breach servers, endpoints, web applications, wireless networks, network devices, mobile devices, and other potential risk points. The process involves gathering information about the target before initiating the test (reconnaissance), identifying possible entry points, attempting to break-in (virtually or genuinely), and reporting the findings. Information on security weaknesses is typically aggregated and presented to IT and network systems management. This allows for formulating strategic conclusions and setting priorities for corrective actions. The main goal of pentests is to identify weak points in system security. They can also be used to test an organization’s compliance with security policies, the security awareness of its employees, and the organization’s ability to identify and respond to security incidents. “Penetration tests are often referred to as “white hat attacks” because it is “the good guys” who try to hack into the system.”

Why conduct penetration tests?

• Security breaches and service interruptions are costly.

Security breaches and any resulting service interruptions or application malfunctions can lead to direct financial losses, damage the organization’s reputation, negatively impact customer loyalty, attract negative media attention, and result in fines and penalties.

• It is impossible to secure all information all the time.

Traditionally, organizations try to prevent breaches by installing and maintaining layers of defensive security mechanisms, including user access controls, cryptography, IPS, IDS, and firewalls. However, the continuous deployment of new technologies, including some of these security systems, has made it even more challenging to identify and eliminate all vulnerabilities in an organization’s security and protect against multiple types of potential security incidents.

• Penetration testing identifies and prioritizes security threats.

Penetration testing assesses an organization’s ability to protect its networks, applications, endpoints, and users from external or internal attempts to bypass security controls to gain unauthorized or privileged access to protected resources.   Frequency of conducting penetration tests: Penetration tests should be conducted regularly to ensure more consistent management of the system and network security. A pentester will reveal how attackers might potentially exploit the identified weakness or emerging vulnerabilities. In addition to regularly scheduled analysis and assessments required by regulatory mandates, tests should also be conducted when:

• New network infrastructure or applications are added
• Significant improvements or modifications are made to the infrastructure or applications
• New office locations are established
• Security patches are applied
• End-user policies are changed

“Being a pentester doesn’t mean being proficient in using tools. Being a pentester means being able to understand how things work, how they are configured, what mistakes people make, and being creative in finding those mistakes. Being a pentester is not just running Metasploit at the entire Internet. It’s something much bigger.” Source: Dawid Balut, How to Become a Pentester and Security Specialist.   Benefits of penetration testing:

• Intelligent vulnerability management

Pentests provide detailed information about real, exploitable security threats. By conducting a penetration test, an organization can actively determine which weaknesses are critical, which are less significant, and which are false positives. This allows the organization to prioritize corrective actions thoughtfully and apply appropriate security fixes.

• Avoiding network downtime

Restoring the system or application after a security breach can cost an organization a lot of money. It is associated with IT repair actions, new protection and customer retention programs, legal actions, etc.

• Meeting legal requirements and avoiding fines

Penetration tests help organizations deal with general aspects of auditing and regulatory compliance. Detailed reports generated by penetration tests can, for example, help organizations avoid significant fines for non-compliance.

• Maintaining a positive company image and customer loyalty

Each individual case of a customer data breach can be costly, both in terms of negative impact on sales and damage to the organization’s reputation. As customer retention costs are higher than ever, no one wants to lose loyal users. Data security breaches can cause not only the loss of loyal customers but also difficulties in acquiring new ones. Penetration tests help avoid incidents that jeopardize the reputation and credibility of an organization. Strategies:

1. Targeted Testing
   Targeted tests are conducted by both the organization’s IT team and the penetration testing team. It is sometimes referred to as the “white-box approach” because everyone has insight into the conducted tests.
2. External Testing
   This type of testing is aimed at external servers or devices of the company, including domain name servers (DNS), email servers, web servers, or firewalls. The goal is to check if an external attacker can gain access and how far they can go once they have access.
3. Internal Testing
   It simulates an internal attack behind the firewall by an authorized user with standard access privileges. This type of test is useful for estimating the potential damage a disgruntled employee can cause.
4. Blind Testing
   The blind testing strategy simulates the actions and procedures of a real attacker by severely limiting information about the attack. Usually, only the company name is provided. This type of test may require a significant amount of reconnaissance and can be costly.
5. Double-Blind Testing
   In a double-blind test, only one or two people in the organization may be aware of the test being conducted. These tests can be useful for testing security monitoring within the organization and identifying incidents as well as response procedures.

Penetration testing is an excellent example of the diversity of the hacking environment. It allows developers to test themselves and provide information about the quality of their code, excluding malicious intentions. Pentests are one of the most potent weapons modern companies have in the fight against cybercrime.