Cyber Insurance – Does it Create More Problems than it Solves?

Welcome to Razorwire, where we and our expert guests tackle the issues and opportunities in the world of cybersecurity. In this episode, we explore the challenges and issues faced by the cyber liability insurance industry.  

This podcast looks into the complex challenges surrounding cyber insurance, an increasingly crucial topic for security leaders and organisations. Join your host James Rees and cybersecurity specialists Chris and Iain, as they engage in an enlightening discussion about the problems with cyber insurance.  

Learn why the dynamic nature of cyber risk has left insurers playing catchup, leading to unfavourable policy terms, skyrocketing premiums and growing frustration for customers. Gain insights into the systemic impacts of ransomware attacks on insurers along with the immense stresses faced by CISOs navigating insurance responsibilities. Discover innovative ideas like continuous security ratings and improved regulations that could transform the broken cyber insurance model.  

Whether you’re a business leader, security professional or just interested in staying informed, this podcast delivers an array of useful take aways to understand the cyber insurance quagmire. Expect an insightful and engaging discussion on this mission-critical topic. Tune in now to stay ahead of the game in the ever-evolving world of cybersecurity. 

And that’s why you’re better off insuring yourself!  

Iain Pye 

Listen to this episode on your favourite podcasting platform: 

In this episode, we covered the following topics: 

  • The challenges insurance companies face in properly assessing and pricing cyber risk due to its constantly evolving nature. 
  • How restrictive policy terms around “acts of war” have made it difficult for companies to receive payouts after attacks. 
  • The lack of cybersecurity expertise and rigorous due diligence conducted by many insurance firms before issuing policies. 
  • The skyrocketing cost of cyber insurance premiums and difficulty obtaining comprehensive coverage. 
  • The problem of companies being unable to get insured after a breach has already occurred. 
  • How the increase in ransomware attacks creates systemic risk for insurers paying out multiple policies. 
  • The stress and burnout faced by CISOs and cybersecurity leaders related to insurance coverage responsibilities. 
  • The importance of cyber defence planning beyond just having an insurance policy. 
  • How continuous security assessment models could help provide better assurance to underwriters. 
  • The need for improved security regulations and standards for the insurance industry to base policies on. 
  • The benefits of self-insuring cyber risks versus relying solely on external insurance. 


Iain Pye 

Iain is a Cybersecurity, Data Protection and Risk Specialist with over 20 years of experience in the public and private sectors. Iain has worked in a range of industries from finance, legal, security and government. When Iain is not fighting fires or arguing personal data ethics, Iain likes exploring the world with his family and occasionally going for a run through the Fens with the dog. If the dog is up for it, which she is usually not.  

Chris Dawson 

Chris Dawson is a former Royal Marine of 11 years. He moved into the private security sector in 2012 taking up various roles across the globe, from hostile environments to the corporate world, advising and implementing security protocols in multiple sectors while gathering and learning as much as possible along the way.   

Resources Mentioned 

UK National Cybersecurity Centre 

Merck insurance payout 

Lloyds of London 

One Trust 

Georgia Cyber Attacks 


Razors Edge Continuous Pen Testing 

Vulcan Files 

Fair Risk Methodology 

Other episodes you’ll enjoy 

Navigating the Turbulent Waters of Cybersecurity: Nationalism, Economics And AI 

Cybersecurity and Critical Infrastructure: Are We Prepared for the Worst? 

Connect with your host James Rees 

Hello, I am James Rees, the host of the Razorwire podcast. This podcast brings you insights from leading cybersecurity professionals who dedicate their careers to making a hacker’s life that much more difficult. 

Our guests bring you experience and expertise from a range of disciplines and from different career stages. We give you various viewpoints for improving your cybersecurity – from seasoned professionals with years of experience, triumphs and lessons learned under their belt, to those in relatively early stages of their careers offering fresh eyes and new insights. 

With new episodes every other Wednesday, Razorwire is a podcast for cybersecurity enthusiasts and professionals providing insights, news and fresh ideas on protecting your organisation from hackers. 

For more information about us or if you have any questions you would like us to discuss email 

If you need consultation, visit, We give our clients a personalised, integrated approach to information security, driven by our belief in quality and discretion. 

Linkedin: Razorthorn Security 

Youtube: Razorthorn Security 

Twitter:  @RazorThornLTD 


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