How Attackers Win: Simulating Real-World Cyber Attacks

I had a conversation with Jane Lo (CyberPenny) in Singapore on 30 April 2026, on how attackers actually win and what it takes for defenders to keep up.

I was in Singapore for a busy week at Marina Bay Sands. I delivered my two-day DEF CON Training, Mastering Breach and Adversarial Attack Simulation Engagements, gave a lightning talk at Milipol TechX (MTX) on adaptive AI assisted ransomware simulation, and presented RedTeamSimmer at DEF CON Singapore Demo Labs.

We talked about how real adversaries operate today, from initial access through to impact; why simulating their attacks tells you far more than guessing; how adaptive AI is changing ransomware and the speed of attacks; what breach and adversary simulation looks like in practice; and why the attacker mindset matters for builders and defenders as much as it does for red teams.

Jane Lo is the Singapore Correspondent for MySecurity Media and hosts the CyberPenny podcast and vodcast, where she talks with people across cyber security, privacy and emerging tech.

Watch it on YouTube. Follow Jane Lo and her CyberPenny channel.

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