Cybersecurity firm Adaptive Security launched a 15-part video training series this week with comedian Conan O'Brien, designed to help office workers recognize and avoid AI-driven threats like fake voice calls, deepfake videos, and convincing phishing emails. The announcement came through PR Newswire on June 9, 2026.

What Is Being Built and Why

The series runs through Adaptive Security's platform and consists of 15 videos hosted by O'Brien. Each module teaches enterprise employees how to spot and respond to social engineering attacks — a term for tactics that trick people into revealing passwords or clicking malicious links — that now use AI. According to Variety, Adaptive Security deliberately chose O'Brien's comedic approach because it wanted to deliver serious security content in a format people would actually want to watch.

The threats covered are real and growing. Voice phishing — tricking someone over the phone by impersonating a trusted person using AI-cloned voices — has become much easier as voice cloning technology improved. Deepfake videos, which used to require significant time and computing power to create, can now be made quickly enough for attackers to use. Spear phishing, a targeted form of email scams aimed at specific people, has been supercharged by AI language models that can write persuasive, grammatically correct messages at scale — removing the telltale signs of poor English that once tipped people off to fraud.

The format is intentional. Traditional corporate security training has a well-known problem: employees often don't complete it or don't remember what they learned. By embedding security lessons into entertaining content, Adaptive Security is betting that people will watch and retain more.

How O'Brien Is Part of the Teaching

Mashable reported that O'Brien uses deepfake humor within the videos — something he has joked about publicly before. This serves a practical purpose. Watching a famous person on screen while learning about deepfakes primes viewers to think critically about whether videos are real. The viewer learns the threat while seeing it demonstrated with someone they recognize.

O'Brien's presence also matters for a demographic security teams struggle to reach: employees who see security training as a chore. A familiar face with comedic talent does not change the actual danger, but it increases the odds that someone will press play and stay through the module.

How This Fits Into the Bigger Picture

Adaptive Security positions itself as a company that both simulates AI-powered attacks and trains employees to handle them. The O'Brien videos are designed to work alongside active practice exercises — meaning trainees both watch and drill against realistic threats. This matches a trend across the security industry: pairing educational content with hands-on simulations to create a complete training loop.

Adaptive Security is part of a wave of startups that launched as generative AI made social engineering attacks cheaper and easier to pull off. Training for voice phishing, deepfake detection, and AI-written spear phishing is now its own product category — separate from older security training companies whose courses were built before these threats existed.

What This Approach Actually Does and Doesn't Do

Content hosted by a celebrity is a distribution strategy — a way to boost engagement. It is not a technical control, meaning it is not a tool that actually blocks an attack. Organizations using this training still need software to detect threats, procedures for responding to incidents, and the organizational practices that keep security as a priority year-round rather than a one-time event.

For IT leaders considering this product, the practical questions matter more than whether the comedy works. What are completion and retention rates. How does it integrate with existing training systems and phishing simulations. Are the scenarios updated as AI improves. Deepfakes and AI voice clones are not static threats; training built today can become outdated within months as the technology gets better and attackers find new tactics.

Looking at the broader context: the security industry has been trying to fix engagement in awareness training for nearly two decades. I covered early versions of game-based and video security training when it first emerged in the mid-2000s — the pitch was the same, that entertainment would improve what people remember. Results were mixed. What is genuinely different now is that the threats themselves — deepfakes, voice clones — are inherently dramatic and easy to show visually in a way that older threats like password rules never were. A video showing a convincing deepfake of a recognizable person making a fraudulent request is compelling in a way a slide about spotting bad links simply is not. Whether that advantage lasts as deepfakes become more common is something the industry will learn through real data over the next few years.

Where to Find It and What to Know

The series launched on June 10, 2026, and is available through Adaptive Security's platform at adaptivesecurity.com/conan. Pricing and licensing terms have not been publicly shared. It is unclear whether the O'Brien series will be sold separately or only as part of Adaptive Security's full simulation platform.

For security and IT professionals, the practical question is whether the content addresses the specific threats relevant to your organization. Voice phishing targeting finance and executive staff, deepfake video used for fraud or impersonation, and AI-written spear phishing are all significant risks for most companies in 2026. A training series that covers all three with production quality high enough to hold attention is a reasonable addition to a layered security program — as long as the content is technically accurate and the scenarios reflect how attacks actually work today.

Bringing in Conan O'Brien is an unusual move for a cybersecurity company. It is also a practical one. Security teams are competing with thousands of other demands for employee attention. Using production value and a recognized voice to win that attention makes sense given what we know about how people learn.