The Four Hidden AI Risks Your Dashboard Won't Show

Join Hack The Box for the first session in AI Has Joined the Security Team, a three-part webinar series on how to secure AI, direct human-agent work and appraise the agents carrying security tasks.

Presented by Hack The Box

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HACK THE BOX WEBINAR SERIES

22 October 2026

  • 2 PM UTC
  • Online
  • Free

Overview

Your dashboard can stay green while judgment, skills, the talent pipeline and agent performance quietly weaken.

As agents become part of security work, leaders need to understand the risks that conventional metrics may not show. Activity can continue. Queues can clear. Reports can look healthy. But underneath, teams may be losing the ability to challenge AI outputs, maintain core skills, develop junior talent or trust that agents are still performing to the expected standard.

In this webinar, Hack The Box CMO Christine Bartlett will be joined by Dimitris Bougioukas, SVP of Training, and Kevin Delaney, Senior Director of Solutions Engineering, to explore the four hidden AI risks security leaders need to watch: automation bias, skill atrophy, the missing middle and silent agentic drift.

The session will also look at how organizations can develop people, exercise teams and appraise agents as part of one connected AI & Cyber Workforce Development strategy.

This is Webinar 1 of AI Has Joined the Security Team: Secure it. Direct it. Score it.