Adaptive Security has partnered with late-night comedian Conan O'Brien to create a 15-video cybersecurity awareness training series that uses humor to teach employees how to recognize and stop AI-powered attacks, including deepfakes, voice cloning, and AI impersonation. The series, filmed in Los Angeles this spring, addresses a critical problem: traditional security training fails to engage employees, with most clicking through compliance modules without retaining the content.

Why Is Security Awareness Training Failing So Badly?

Organizations spend billions annually on cybersecurity training programs, yet employees tend to forget the material before their next login. The problem has only worsened as attack tactics evolve faster than the training designed to address them. In 2025, Adaptive reported that more than half of its enterprise customer conversations included firsthand accounts of deepfake attacks inside their organizations. Deloitte projects that AI-facilitated fraud losses in the U.S. will grow from $12.3 billion in 2023 to $40 billion by 2027.

The gap between threats and defenses is widening. Voice phishing, deepfake personas, and AI-generated impersonation are hitting companies every week, yet most training programs were built years before these attacks existed. This is where O'Brien's involvement becomes strategically relevant. His signature absurdist humor and deadpan delivery train employees to slow down and look twice before acting, directly countering the urgency and panic that AI-powered attacks manufacture.

How Does Comedy Actually Defend Against AI Threats?

Each of the 15 training modules opens with a comedic O'Brien introduction that frames the cybersecurity threat in a way employees are unlikely to forget. Adaptive's existing instructional material, interactive elements, and knowledge checks follow each introduction without modification. Security teams can choose to assign either the standard version or the Conan version to employees, giving them full control over their training approach.

O'Brien's voice and likeness are themselves relevant to the subject matter. The same AI tools that power modern deepfake attacks can clone his voice and face with ease. Adaptive estimates that up to 60% of employees fail AI-powered attack simulations without prior training, highlighting the scale of the knowledge gap.

"Voice phishing, deepfake personas and AI-generated impersonation are hitting companies every week, and most training programs were built years before those attacks existed. We wanted to build something personal and engaging, something employees would actually look forward to," said Brian Long, CEO and co-founder of Adaptive Security.

Brian Long, CEO and co-founder of Adaptive Security

Adaptive's co-founder Andrew Jones explained the stakes to Variety: "There's really a before and after. There's the before, which was pre-AI, and then there's the after, which is after AI, and after AI, these attacks have gotten much more sophisticated. There's a lot more of them, they're much harder to detect and remediate, so it's already a huge problem".

Andrew Jones

What Specific Threats Does the Training Cover?

The training series addresses two categories of security awareness content. The first focuses on AI-powered attacks driving the fastest growth in incidents today, while the second covers foundational topics that remain critical to corporate security.

• AI-Powered Attacks: Deepfakes, voice cloning, and AI impersonation that use generative AI tools to create convincing fraudulent communications and bypass authentication systems.
• Traditional Threats: Email and SMS phishing, QR code scams, password vulnerabilities, and physical security risks that remain prevalent despite years of awareness campaigns.
• Remote Work Risks: Security gaps created by distributed workforces, including unsecured home networks, shared devices, and reduced visibility into employee behavior.

O'Brien's team co-wrote the scripts with Adaptive and improvised on set, bringing his signature smart and silly comedic instincts to each topic. The comedian himself noted the partnership's appeal: "I teamed up with Adaptive Security just to figure out what these kids are up to. Turns out it's pretty cool".

How to Build Effective Security Awareness Training

Organizations looking to improve their security training effectiveness should consider several key principles that Adaptive's approach demonstrates:

• Engagement Over Compliance: Move beyond checkbox training that employees tolerate to content they actually want to watch. Humor, storytelling, and relatable scenarios increase retention and behavior change.
• Relevance to Current Threats: Update training materials to address emerging attack vectors like deepfakes and voice cloning, not just legacy phishing tactics. Training built years ago cannot address threats that didn't exist then.
• Flexibility in Delivery: Offer multiple versions of training content so security teams can customize assignments based on employee roles, risk levels, and organizational priorities.
• Behavioral Psychology: Use humor and absurdism to counteract the panic and urgency that attackers deliberately manufacture. Employees who slow down and think critically are less likely to fall for social engineering.

The training series is immediately available to Adaptive's current enterprise customers and comes included for any organization that joins the platform. Organizations interested in accessing the training can visit adaptivesecurity.com/conan.

What Makes This Partnership Newsworthy for Cybersecurity?

Adaptive Security, co-founded in 2024 by Brian Long and Andrew Jones, has raised over $140 million from investors including Bain Capital Ventures, Andreessen Horowitz, NVIDIA Ventures, and OpenAI Startup Fund. The company defends more than 1,000 enterprise customers against AI-powered attacks and offers a platform that includes security awareness training, phishing simulations, email security, AI governance, and risk scoring.

The O'Brien partnership reflects a broader industry shift: as AI-powered attacks become more sophisticated and prevalent, organizations are rethinking how to prepare employees to recognize and resist them. Traditional compliance-driven training has failed to move the needle. By recruiting a world-class entertainer to make security awareness engaging and memorable, Adaptive is betting that behavior change requires more than fear and obligation.

The stakes are real. Deepfake fraud surged by 1,100% in recent years, and synthetic identity document fraud rose by over 300% in the United States alone. In one case, an Indonesian financial institution was the victim of 1,100 deepfake attacks to bypass their loan application service, resulting in a financial impact estimated at $138.5 million. These numbers underscore why organizations need employees who can actually recognize and resist these threats, not just employees who have clicked through a training module.