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Navigating Threats: Adopting Proactive Social Engineering and Network Testing Strategies

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On average, organizations are targeted by over 700 social engineering attacks each year, according to Barracuda’s Spear Phishing: Top Threats and Trends report. These attacks are designed to exploit human nature, manipulate emotions, and trick individuals into divulging sensitive information that help hackers achieve their goals.

Bishop Fox hosted a fireside chat webcast, Combatting Adversaries: Proactive Social Engineering and Network Testing, with our offensive security experts, Senior Security Consultant Alethe Denis, Managing Principal Ben Lincoln, Senior Security Consultant Derek Rush, and Principal Researcher Rob Ragan. They shed light on the importance of understanding social engineering tactics and strategies, implementing technical controls, and the key role of internal network testing in creating a powerful cybersecurity infrastructure. You can get webcast highlights in this blog, and don’t forget to tune in on demand!

Setting the Stage for Social Engineering

Social engineering is a proven strategy employed by hackers to exploit the human element in cybersecurity defenses. In the realm of social engineering, understanding human psychology is paramount. Our security experts explain that the success of this tactic often lies in attackers' ability to appear helpful, friendly, and likable, enabling them to bypass an organization's defenses and gain the trust of unwitting employees. To uncover more about this pervasive threat, our experts delve into their experiences with social engineering in penetration testing engagements and uncover the factors that make them highly lucrative.

Like other attack tactics, targeted spear phishing has advanced and evolved alongside the rapid expansion of digital technologies. Engaging users through emails and subsequently following up with phone calls, attackers leverage their established trust to trick users into running malicious software. This method capitalizes on the inherent trust users often place in those claiming to possess knowledge in a particular domain.

One example that proved successful for our penetration testers that exemplifies the simplicity and effectiveness of social engineering involves posing as a newly onboarded employee seeking technical support. By obtaining the employee's start date from social media platforms, attackers easily manipulated the situation, leading the help desk to disclose sensitive information without hesitation and enabling an assumed breach simulation.

Interestingly, our experts encountered an engagement where fear-based tactics were prohibited by the client, which proved to be an advantageous approach. Acting as a friendly IT staff, penetration testers aimed to enhance the employees' experience with logging on, accessing credentials, and other tasks. This helpful demeanor enabled a successful social engineering exercise, exploiting the trust between the attacker and the targeted individuals.

The convergence of technology and human psychology necessitates constant vigilance and a proactive approach to safeguarding sensitive information.

The Rising Threat of AI-Powered Social Engineering

With the rapid advancements in AI and machine learning, the landscape of social engineering is undergoing profound changes. One of the key developments is the ability to generate seemingly legitimate, customized content for each interaction and even for each user. This has created a tipping point, necessitating the development of new tools that can detect and counter these emerging issues with improved efficacy.

A recent disturbing case involved the utilization of generative AI in an extortion scam. Perpetrators leveraged this technology to create an audio recording that mimicked the voice of the victim's own daughter, falsely claiming that she had been kidnapped. This incident highlights the immense power that attackers now wield, as just a two-minute audio recording is sufficient to create convincing and manipulative AI-generated content. The implications are far-reaching, from demanding ransom to extorting victims.

The concerning reality is that even a person's social media presence can be analyzed and used by certain tech stacks to predict the likely phrases they would use in their speech or writing. As technology becomes more commoditized and widely available, such nefarious activities are likely to increase in prevalence.

The need for robust defense mechanisms and continuous innovation in detection and prevention methods has never been more evident. By understanding the capabilities and potential risks associated with AI and machine learning, the cybersecurity community can work towards creating a safer digital environment.

Scenario One: Phishing and Ransomware

One of the first scenarios our experts explored was based on a real-life attack, where a phishing email led to a ransomware incident. Utilizing MITRE-ATT&CK controls, our experts showcased how organizations can enhance security and detection at each attack stage for the specific scenario.

In this scenario, attackers gained initial access through a spear phishing email with malicious macros in a Word document. Once inside, attackers explored the victim's infrastructure to find privileged access points. Mitigating this is challenging as the attackers operated undetected, looking like legitimate users. Detecting data theft is also difficult, as it appears as normal employee behavior. Behavioral analytics and anomaly detection can help in identifying unusual user commands or programs, but they aren’t foolproof. To prevent lateral movement, segmenting networks and applying least privilege at the host level is highly effective. Limiting employees' access reduces their attack surface if their credentials are compromised.

Ransomware attacks are not simple; however, relying on technical controls at different stages can minimize malicious actors' access. Operating with a 'not if, but when' mindset, organizations should have an incident response policy and plan. Regular tabletop exercises ensure instant access to and activation of the disaster recovery plan after an attack, helping enhance cybersecurity resilience.

Scenario Two: Insider Threats

Insider threats can take on various forms, including the typical malicious insider as well as unwitting individuals who unknowingly cause harm. It's important to recognize that anyone can become an insider threat given the right means, motive, and opportunity. And social engineering can play a significant role in insider threat scenarios.

Managing sensitive data, data classification, and controlling access to key information are complex challenges. Strictly enforcing the principle of least privilege and utilizing host-based controls can significantly reduce insider threats. Unfortunately, this is often not accomplished to its maximum potential.

Implementing tools like honey pots or tokens in your network can assist in monitoring and triggering incident response when unauthorized interactions occur. By overlaying detective controls on the real environment, insider threats can be effectively detected. Creating an alert system to identify these anomalies is also crucial for incident response.

Enhance Your Security with Red Teaming and Network Testing

In today's unpredictable landscape, attackers know no limits. That's why your testing should be equally boundless. Red Teams can covertly execute finely crafted attacks to truly measure the effectiveness of your security teams.

Take advantage of advanced Red Teaming by incorporating social engineering tactics, incident response tabletop exercises, and ransomware readiness. This comprehensive approach will ensure that your defenses are ready for whatever comes their way.

When it comes to network testing, it's vital to understand how skilled adversaries can infiltrate your systems and put your sensitive data at risk. Whether it's external penetration testing or attack surface management, these offensive security services provide valuable insights and identify any dangerous exposures. With a thorough pressure test of your perimeter defenses, organizations have tangible knowledge that they’ve prepared for any cybersecurity eventuality.

But it wouldn’t make sense to only test the perimeter. It is critical to pressure test for assumed breaches, too. Internal penetration testing goes deep to uncover any vulnerable systems, pathways, and data that could be at risk if attackers manage to break through. With the meticulous approach that penetration testing offers, no stone is left unturned, ensuring that an organization’s entire infrastructure is fortified and safeguarded.


Don't wait for a potential breach to expose your vulnerabilities. Take proactive steps now and elevate your security with Red Teaming and network testing.

Check out this list of resources to keep your organization ahead of social engineering attacks:

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About the author, Beth Robinson

Senior Content Writer

Beth Robinson is a Senior Content Writer at Bishop Fox. She joins Bishop Fox with nearly 20 years of experience focused on technical intelligence issues.

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