Offensive Security Services: How to Improve Security by Thinking Like an Adversary

Taking a proactive approach to cybersecurity is essential for safeguarding sensitive data and systems from potential threats. By adopting an offensive security strategy, organizations can identify and mitigate vulnerabilities and risks before they are exploited by malicious actors. 

Thinking like an adversary in offensive security services involves constantly adapting to the ever-changing threat landscape. By staying one step ahead of potential attackers, security professionals can better protect sensitive data and infrastructure from both known and unknown threats. This proactive and strategic approach not only enhances the overall security posture of an organization but also demonstrates to customers and partners that a commitment to cybersecurity is a priority.

What Is Offensive Security?

Offensive security (OffSec) takes an adversarial approach to cyber defense, in which organizations simulate the tools and tactics used by genuine adversaries to assess the resilience of their security controls. To put it simply, the concept of offensive security embraces the idea that attack is the best form of defense.

To more accurately replicate the conditions of a genuine attack, offensive security services are often performed by a third party, rather than by an organization’s in-house security team. This is done to ensure that the in-house team receives unbiased feedback regarding their security posture and allows them to understand how an outside attacker would identify and leverage security gaps. Some of the most common forms of offensive security services include penetration testing, red team exercises, vulnerability assessments and social engineering.

Penetration testing involves conducting a thorough assessment of system vulnerabilities to identify potential weaknesses that could be exploited by malicious actors. This process typically involves using a variety of tools and techniques to simulate attacks and uncover any security gaps that need to be addressed. By proactively identifying and addressing vulnerabilities, organizations can better protect their systems and data from potential cyber threats.

On the other hand, red team exercises take a more aggressive and targeted approach by simulating real-world attacks on an organization’s systems and networks, over a longer period. This type of offensive security service goes beyond simply identifying vulnerabilities. Red teaming exercises go deeper, exploiting vulnerabilities to determine the scale of damage and disruption that could be inflicted by a real cyberattack. By more closely mimicking the conditions of a genuine cyberattack, red teaming helps organizations better understand their security posture and readiness to defend against sophisticated adversaries.

Vulnerability assessments serve a fundamental function within an offensive security program, as they involve the systematic identification and analysis of weaknesses in computer systems, networks and applications. This process typically involves using specialized tools and techniques to scan and probe systems, looking for known vulnerabilities that could be exploited. While vulnerability assessments can be performed on their own, they are often used as a preliminary step for deeper offensive security activities.

Social engineering is another foundational component of offensive security, focusing on exploiting vulnerabilities caused by human behavior rather than only technical weaknesses. This technique involves manipulating individuals through psychological tactics, deception and persuasion to gain unauthorized access to sensitive information or systems. Social engineering attacks can take various forms, such as phishing emails, impersonation or pretexting, and they often rely on exploiting human trust and naivety. By understanding and leveraging human behavior, offensive security professionals can gain access to valuable information or compromise systems, highlighting the importance of security awareness training.

Offensive Security Tools

Offensive security encompasses a range of techniques and strategies aimed at identifying and exploiting vulnerabilities in systems and networks. However, for an OffSec team to be effective, they also rely on a wide range of industry tools to execute a thorough assessment of an environment and strengthen the security of networks and systems.

Network scanning tools like Nessus and Nmap are commonly used to identify vulnerabilities and potential entry points in a network. By conducting thorough scans, security experts can pinpoint weaknesses that can be exploited as part of an assessment.

Exploitation frameworks such as CANVAS are powerful tools that enable security professionals to simulate cyberattacks and test the resilience of systems against various threats. These frameworks provide a platform for executing exploits and gaining unauthorized access to systems.

Password cracking tools like John the Ripper and Hashcat are instrumental in testing the strength of passwords and encryption methods. By using these tools, security professionals can assess the effectiveness of password policies and encryption techniques.

Additionally, wireless hacking tools like Wireshark and application testing platforms like PortSwigger’s Burp Suite play a crucial role in identifying and addressing security weaknesses in wireless networks and web applications, respectively.

Offensive Security Certifications

Offensive security certifications serve as a validation of an individual’s knowledge in offensive security practices. They are designed to equip professionals with the necessary skills to identify vulnerabilities, exploit them ethically, and implement effective security measures. While certifications are not a stand-alone indicator of a security professional’s skills and abilities, by obtaining offensive security certifications, individuals demonstrate their commitment to staying ahead of cybercriminals and their ability to safeguard organizations against potential attacks.

When it comes to popular offensive security certifications, three notable ones stand out: OSCP (Offensive Security Certified Professional), CEH (Certified Ethical Hacker) and GPEN (GIAC Penetration Tester). OSCP is highly regarded for its hands-on approach, requiring candidates to complete a challenging 24-hour practical exam. EC-Council’s CEH certification focuses on ethical hacking techniques and methodologies, covering a wide range of topics such as network scanning, system hacking and social engineering. GPEN, offered by GIAC, validates professionals’ skills in conducting penetration tests and identifying vulnerabilities in networks and systems.

Employers often prioritize candidates with specific offensive security certifications, as they provide assurance that the individual possesses the necessary skills to conduct more rigorous assessments, adapt to a changing threat landscape and deliver tangible security outcomes to customers.

What to Look for in an Offensive Security Vendor

When selecting an offensive security vendor, it is critical to carefully evaluate the expertise and experience of the vendor’s team. The effectiveness of the security measures implemented by the OffSec vendor will largely depend on the knowledge and skills of their team members. It is important to ask about the offensive security certifications of the team members, the depth of their experience and their track record in successfully handling security incidents.

Another important factor to consider is the range of services offered by the offensive security vendor. Different organizations have varying security needs, so it is essential to choose a vendor that can provide a comprehensive suite of services to build assessment programs that are tailored to the needs of each one.

Reputation in the form of case studies and testimonials can support the decision-making process. A vendor with a strong track record of successful engagements and positive feedback from satisfied clients is more likely to deliver high-quality services and meet your security needs effectively.

It is essential that the vendor follows best practices and adheres to relevant regulations to ensure that your organization’s security requirements are met. CREST accreditation is a useful seal of approval. Be wary of organizations offering unusually low, or “too good to be true,” pricing without CREST certification to back up their claims.

Why Kroll?

Kroll provides a comprehensive suite of proactive cybersecurity solutions designed to detect and mitigate potential risks to a company’s digital framework. Our array of services encompasses penetration testing, vulnerability assessments and red team exercises, all of which simulate genuine cyberattacks to harden organizations’ cybersecurity posture.

By leveraging the collective expertise of our offensive security, threat intelligence and risk assessment teams, along with our extensive experience in handling over 3,000 incident response (IR) cases each year, we provide unparalleled support to:

• Seamlessly discover and address key vulnerabilities in line with your organization’s expanding attack surface.

• Uncover previously unknown risks throughout your digital presence and minimize vulnerabilities across all levels.

• Conduct red teaming and penetration testing led by experts, utilizing tactics gained through our industry-leading incident response services to deliver tailored attack simulations.

• Enhance security monitoring efficiency with purple teaming collaborations, resulting in nearly 50% higher detection coverage on average.

• Address detection and response deficiencies, while enhancing security protocols, policies and technical measures.

With Kroll’s comprehensive approach to offensive cybersecurity, organizations can stay ahead of cyber threats and safeguard their critical assets from potential attacks.