What is Offensive Security and Why is it So Challenging?

In cybersecurity, offensive security involves proactively simulating a cyber attacker’s behavior to identify system vulnerabilities. By understanding these potential vulnerabilities, organizations can then implement and enhance security controls to reduce the risk of exploitation by actual malicious actors.

Offensive Security Methods

The three major approaches to offensive security are:

• Vulnerability Assessment: The automated identification of weaknesses using scanners
• Penetration Testing: The simulation of cyber attacks to identify and exploit vulnerabilities
• Red Teaming: The simulation of complex, multi-stage attacks to test detection and response capabilities

These approaches share similarities but differ in various aspects, as shown in the table below.

Offensive Security Testing Practices

Phases of Offensive Security Engagements

While the techniques and depth of testing vary across offensive security engagements, they typically follow the same five phases:

• Reconnaissance: Gathering extensive data regarding the target's systems, networks, and organizational structure
• Scanning: Examining identified systems to uncover critical details such as live hosts, open ports, and running services
• Vulnerability Analysis: Identifying potential security weaknesses within systems, software, network configurations, and applications
• Exploitation: Exploiting identified vulnerabilities to gain unauthorized access or escalate privileges within a system
• Reporting: Compiling all findings into a detailed report

Current Challenges in Offensive Security

Offensive security testers navigate an increasingly complex landscape, facing numerous challenges that can hinder the efficiency and effectiveness of their assessments, including:

Expanding Attack Surface: New technologies, such as AI, blockchain, cloud computing, and IoT, have greatly expanded the attack surface. This makes it harder to identify and secure all potential entry points.

Advanced Threats: Adversaries are employing more sophisticated techniques that can be difficult to detect and mitigate.

Diversity of Assessments: Offensive security teams must be proficient in conducting a wide range of assessments. Each type demands specific skills, techniques, and knowledge, making it difficult for testers to maintain expertise across all domains.

Adapting to Dynamic Environments: Offensive security assessments often occur in dynamic environments where target systems, security controls, and configurations change rapidly. Testers must remain agile and adapt in real-time.

Balancing Automation and Manual Testing: Automated tools are essential for efficiency, but over-reliance can lead to missed vulnerabilities and distraction by false positives. Striking the right balance between automated scanning and in-depth manual analysis is key.

Time-Consuming Tasks: Certain tasks often involve extensive reconnaissance and iterative exploitation attempts. Examples include comprehensive authorization testing, code reviews, crafting spear-phishing emails, and exploitation of complex vulnerabilities.

Tool Development and Customization: Unique vulnerabilities and target environments often require offensive security testers to develop or adapt their scripts, tools, and frameworks.

Communication and Reporting: Communicating technical findings, translating them into actionable recommendations, and delivering concise reports can be challenging. This is particularly true when there is a substantial knowledge gap between testers and their audience.

Data Analysis and Threat Intelligence: The sheer volume of data generated during an assessment can be overwhelming. Extracting insights, correlating findings, and staying up-to-date with threat intelligence demands constant vigilance and advanced techniques.

Compliance and Ethical Considerations: Testers must adhere to a growing number of strict security standards, regulations, and ethical guidelines. This can be resource intensive and time consuming.

Mitigating Challenges with AI-Powered Offensive Security

AI, particularly large language models (LLMs), offers promising avenues for addressing many of the above challenges. AI-powered tools can:

• Simulate advanced cyber attacks and cover a broader range of attack scenarios
• Identify network, system, and software vulnerabilities
• Respond dynamically to vulnerability findings
• Adapt to different environments and improve over time
• Aid security teams in scaling their efforts
• Generate and execute unseen test cases
• Process vast amounts of data
• Uncover patterns that humans can’t recognize
• And more

A recent publication from CSA’s AI Technology and Risk Working Group further explores these applications. Get an in-depth look at offensive cybersecurity and its current challenges, as well as the many ways AI can help.

Download your free copy of Using AI for Offensive Security.