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EP 202: Why Fortune 500s Still Run on Windows 2003 artwork
Cyber Risk Management Podcast

EP 202: Why Fortune 500s Still Run on Windows 2003

  • E202
  • 38:15
  • January 27th 2026

Why do IT organizations cling to ancient technology like Windows 2003, creating dangerous technical debt they don't even recognize? And how do they get out of this trap? Let's find out with our guest Anton Chuvakin, who advises the biggest customers of Google's Cloud services. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

 

LinkedIn profile -- https://www.linkedin.com/in/chuvakin/

 

Podcast -- https://cloud.withgoogle.com/cloudsecurity/podcast/

Cyber Risk Management Podcast

Cyber risk made clear for busy leaders. Cyber threats move fast. Your business must move faster. In every episode, Kip Boyle—author of "Fire Doesn’t Innovate" and CISO at Cyber Risk Opportunities—joins cybersecurity attorney and CISSP Jake Bernstein to break down the latest cyber risk. You’ll hear plain-English explanations of what's going on and what you need to do about it. No jargon. No doom. Just clear steps you can use today to save money, win buy-in, and stay out of the headlines.