AI for Good and Evil

How Webcheck Security Uses AI in Penetration Testing and How Threat Actors Adapt

AI-Enhanced Information Gathering

Webcheck Security’s penetration testers have integrated AI into their information gathering workflows to rapidly parse large datasets and identify high‑value insights. This mirrors industry findings where AI assists in reconnaissance and pattern recognition, including attackers using adaptive ML models to automate data gathering.

Practitioners at Webcheck Security also use AI to better understand vulnerabilities and recommended remediations, enabling more accurate prioritization during test engagements. This is consistent with broader trends in cybersecurity research showing how AI can streamline analysis and accelerate exploit discovery timelines.

AI for Tooling and Exploitation Support

AI also assists Webcheck testers with building internal tooling capable of summarizing logs, detecting anomalies, and flagging attack paths that might otherwise remain hidden. These capabilities align with advancements documented in industry threat reports, where defenders and attackers leverage AI for complex behavioral analysis.

Furthermore, AI-driven insights allow testers to simulate more realistic post‑exploitation scenarios that resemble actor behaviors observed in the wild. This is validated by reporting on AI‑powered malware demonstrating adaptive behavior and dynamic execution.

How Threat Actors Leverage AI

Webcheck Security experts have observed that threat actors now use AI to generate highly evasive malware far more quickly than before, reducing the skill barrier significantly. Public analysis confirms that malicious actors increasingly integrate generative AI to mutate malware in real time and evade detection.

Similarly, attackers use AI to build or enhance post‑exploitation frameworks, including C2 infrastructure designed to operate stealthily under encrypted protocols. Studies on encrypted C2 traffic validate the rise of AI‑supported communications built to blend seamlessly into legitimate network activity.

AI‑Driven Social Engineering and Phishing

Webcheck testers emphasize that AI now enables threat actors to craft highly realistic phishing emails, tailoring tone and content to specific targets. Research indicates that attackers use LLMs to generate nuanced phishing lures, supporting both nation‑state and criminal operations.

Advanced AI‑enabled attacks can also produce personalized messages and documents at scale, mimicking legitimate correspondence in ways previously unattainable. Examples include deepfake‑driven social engineering campaigns that have already led to major financial losses.

Read more about Webcheck Security’s innovative, fast, and thorough approaches to penetration testing and cybersecurity at our blog, or contact us today to discuss your next penetration test using our best-in-class testing team!