Preemptive Power: How Offensive Security Shapes Cyber Resilience

As I continue writing articles about strategic deployment of a robust and lean cybersecurity program, this article will focus on building an Offensive Security Program. Cyber threats are evolving with alarming speed and complexity, organizations must arm themselves with an arsenal of proactive strategies to defend their critical assets. Gone are when passive defense mechanisms were sufficient. Today’s cyber warriors must adopt offensive security measures—such as penetration testing, red teaming, purple teaming, and threat hunting—to actively seek out and neutralize threats before they strike. But at the same time testing people, processes, and technology which is a form of assurance that all components are doing what they should be doing. These proactive approaches not only enhance an organization's defensive capabilities but also prepare them to anticipate and counter cyber threat actors effectively. By integrating these offensive strategies into their cybersecurity framework, businesses can turn the tide against attackers, transforming their security posture from reactive to predictive. This article explores the multi-layered approach necessary to fortify defenses and ensure resilience in an ever-shifting cyber threat landscape, providing a strategic blueprint to safeguard your organization’s future with an intelligence-driven framework and vision to harness and focus the team’s efforts.

Understanding Threats

As a CEO or CISO, it is imperative to ensure your team is well-informed about the cyber threat actors that pose a risk to your organization so you can implement effective defensive and proactive measures. This not only protects your business operations but also maintains the trust of your customers. Here is a high-level overview of the types of threats you should be aware of:

• Nation-States: Countries using cyber tactics to gather intelligence for political, military, and business advantages.
• Cybercriminals: Individuals or groups primarily focused on financial gain through cyber activities.
• Hacktivists: People motivated by ideological causes, using hacking as a tool to promote their agendas.
• Insider Threats: Trusted individuals within your organization who may have access to sensitive information and could potentially exploit it.
• Hybrid Threats: A combination of any of the above actors, complicating detection and response strategies.

Common Methods of Attack

The initial access vectors used by these actors vary, but the most common include:

• Email Phishing: The primary method for delivering malicious links or attachments to steal credentials or deploy malware.
• Server Exploits: Targeting high-value servers with database exploits to gain unauthorized access.
• Software and Hardware Vulnerabilities: Exploiting flaws in programs and hardware to infiltrate systems.
• Credential Theft: Using stolen or purchased credentials to impersonate legitimate users.

Specific Security Tools Need to be Deployed First

Before we delve into proactive offensive security, it's crucial to understand the foundational security tools necessary for an effective Offensive Security Program. I am vendor agnostic and won't recommend specific products, but here's an overview of essential tools required to ensure your program operates at full capacity:

• Endpoint Detection & Response (EDR): Advanced endpoint protection technologies, including next-generation antivirus, to guard against emerging threats.
• Network Security Tools: Intrusion Detection Systems (IDS), Intrusion Prevention Systems (IPS), advanced firewalls, and network segmentation to safeguard sensitive data.
• Security Information and Event Management (SIEM): A central system for aggregating log data, which is crucial for comprehensive monitoring and response.
• Email and Web Security:Solutions to protect against phishing, malware, and other web-based threats.
• Identity and Access Management: Technologies to ensure that only authorized users can access your resources, which is particularly important for protecting against insider threats and identity fraud.
• Cloud based: Tools that function effectively in cloud environments to manage and analyze data logs, essential for businesses utilizing cloud storage and services.
• Unified Ticketing System: To maximize efficiency and track effectiveness across your cybersecurity program—and ideally across your entire organization—it's best to use a single ticketing system. This prevents fragmentation and enhances the ability to measure success.

Selecting the Right Tools

When selecting security tools, start by defining your specific needs based on your business objectives. Ensure that any new tool aligns with your existing processes and minimizes the introduction of new workflows. Additionally, consult your Cyber Threat Intelligence (CTI) Team to assess any vulnerabilities linked to the tools, such as country of origin or other security concerns that might affect your operations. Of note, engineering teams who drive the requirements or tool selection for the SOC, Threat Hunting or your CTI Teams, is an ill-advised proposition. Intelligence drive operations!

For example, consider an instance where I was part of a team that bought and deployed a new security tool. Despite high expectations, the tool was not deployed or connected to other systems, rendering it almost useless—a costly and ineffective outcome. This was primarily driven by the engineering team. This underscores the importance of not only selecting tools that meet the functional needs of your teams, such as infrastructure or engineering, but also ensuring these tools integrate seamlessly into your existing technology stack.

Testing Tool Effectiveness

It's vital to conduct a Proof of Concept (PoC) or Proof of Value (PoV) to test the tool's functionality within your specific environment. This hands-on evaluation helps confirm whether the tool integrates without disrupting existing processes or security measures. Known as Software Assurance, this process ensures the tool is free from known vulnerabilities and performs as promised.

Organizational Structure

In my previous posts, I've touched upon organizational structure for two key reasons. First, the necessity for teams to have access to a higher level of information from other teams; without this, their core functions can be significantly diminished. Second, to prevent the formation of silos. Having worked with dozens of organizations, I've seen firsthand how rampant silos can negatively impact the value of security efforts—they may keep teams busy, but not necessarily effective or value-adding.

For offensive security to deliver maximum value, it must be led with an intelligence-driven approach. Understanding the cyber threat landscape and the key actors involved is crucial, and this information typically stems from your CTI Program. Therefore, your Offensive Security Program should be integrated within your CTI Function to enhance coherence and effectiveness.

In a future article, I will delve deeper into what this integrated structure looks like and how it functions within larger organizations, providing a blueprint for enhancing security posture through strategic organizational alignment.

Teams and overall functionality

Penetration Testing

This team is essential for testing both externally facing and internal applications, especially targeting your high-value servers and databases. It's crucial to employ both Static Application Security Testing (SAST) and Dynamic Application Security Testing (DAST) to assess security both pre-deployment and during runtime. Effective collaboration with your CTI Team is vital to align with the latest cyber threat landscape trends.

Threat Hunting

Consider this team as your cyber detectives, tasked with determining whether any unauthorized activity has occurred—or may still be occurring—within your network. Their operations are primarily directed by insights from your CTI Team. Without a CTI Team, your Threat Hunters may lack the necessary context to effectively prioritize and address threats.

Red & Purple Teams

Red Team

Drawing from military terminology where Red signifies the 'enemy,' this team simulates the tactics, techniques, and procedures of top cyber threat actors of concern within your industry. The primary goal is to rigorously test your people, processes, and technology to ensure your security posture is robust. Executive approval is required for these exercises, and the details of these tests are intentionally kept confidential from the Blue Team—your network defenders and incident responders—to gauge their real-time reaction to simulated attacks.

Purple Team

This involves a collaborative effort where the Blue Team is informed and works directly with the Red Team. The focus here is on ensuring that your security controls are effectively detecting threats. This capability can typically be automated for efficiency.

SMBs Recommendation

Most of this article is focused on large organization that have both money and people to create an offensive security program. The following are recommendations tailored for SMBs to stay on top of the latest threats and take proactive steps to engage and communicate with your vendors.

• Leverage Outsourced Expertise: Consider hiring external cybersecurity consultants or managed security service providers (MSSPs) who specialize in offensive security. These providers can perform regular penetration tests, vulnerability assessments, and security audits to identify and mitigate potential vulnerabilities without the need for an in-house team.
• Prioritize Basic Cyber Hygiene: Ensure that fundamental security practices are in place, such as strong password policies, multi-factor authentication, regular software updates and patch management, and secure configurations of networks and devices.
• Security Awareness Training: Educate employees about common cyber threats like phishing, social engineering, and safe internet practices. This can significantly reduce the risk of human error, which is often the weakest link in cybersecurity.
• Engage with Cybersecurity Communities: Join local or industry-specific cybersecurity groups and online forums where you can gain insights, share best practices, and stay updated on the latest security trends and threats. These communities can also provide support and resources for SMBs.
• Use Open-Source Tools: Consider using open-source security tools that can be customized to fit your needs at a lower cost than commercial products. Many open-source tools have robust user communities and documentation to help with setup and maintenance.

By focusing on these areas, SMBs can build a strong defensive posture and mitigate many of the risks associated with cyber threats, even without an offensive security team.

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Dewayne Hart CISSP, CEH, CNDA, CGRC, MCTS Benjamin Edelen Mark Davenport, M.S., CISSP Cristian Julius 🔒Ivette B. Mari Galloway, M.S.I.S, CISSP James Trainor Pete Cordero CPA, CISSP, CISA, FBI (Ret.) Daniel Yocca (FBI Retired) Peter V. Michael Goodman Ben Ouano Sherry P. Jessica A. Robinson (She/Her)