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Admission Tickets FREE for
Premium Members
Admission tickets at $149 for free members
A premier education and networking event, this online bootcamp features four short workshops and one expert panel discussions by leading cyber experts who share their insights on technical risks and market shifts that will define 2026.
This isn’t another pay-to-play conference. Our speakers and agenda has been handpicked – no sponsored slots, no sales pitches, just unbiased, distilled, expert insights.
All participants will receive a digital Certificate of Participation from the Cyber Insurance Academy.
Use it as proof of your up-to-date technical knowledge and share it with your professional network or on LinkedIn to highlight your commitment to staying ahead in the fast-moving world of cyber insurance.
The Cyber Insurance Bootcamp features leading experts from cyber insurance, cybersecurity, and risk management delivering in-depth sessions on emerging risks and evolving technical trends.
Our agenda is carefully curated for to ensure our members are fully briefed and ready to hit the ground running in 2026. It has not shaped by sponsors or commercial interests. Every session is led by experts selected for their unbiased insight and technical expertise, and the schedule below is set to ensure a focused, high-value experience for all attendees.
15:00-15:05 (GMT +1)
Guy Simkin
CEO and Co-Founder
Cyber Insurance Academy
A brief welcome from Cyber Insurance Academy’s CEO, Guy Simkin, introducing the Bootcamp’s goals, themes, and what participants can expect from this year’s deep-dive sessions on the technical risks redefining cyber insurance.
15:05-15:35 (GMT +1)
Jay Vinda
Group CISO & Risk Engineering Lead, Cyber
Mosaic
Winning a CISO’s trust is no easy feat, much less selling them a cyber insurance policy. They are often skeptical, pressed for time, and laser-focused on risk in business terms, not insurance jargon.
This session pulls back the curtain on how CISOs really think about cyber insurance: what frustrates them, what wins their trust, and how brokers and underwriters can finally bridge the gap between technical risk and business value. Expect practical takeaways on how to reframe conversations so CISOs see you as a partner, not a hurdle.
Jay has lived on both sides of the table – a CISO and now as an insurance insider shaping how policies meet real cyber risk. He knows exactly what resonates with CISOs and how insurers can adjust their approach to earn credibility and trust.
15:40-16:10 (GMT +1)
Tony Anscombe
Chief Security Evangelist
ESET
From state-sponsored intrusions, AI-powered malware, deception and social engineering campaigns to targeted attacks from groups like Scattered Spider; cyber attackers have spent 2025 testing the limits of what’s possible. Nation-state operations have grown more sophisticated, specifically targeting the utility sector and blurring the line between cyber and physical warfare.
This session will unpack how threat actors have sharpened their tactics – from leveraging AI for precision attacks to exploiting human vulnerabilities in new ways. Tony will dissect how these attacks unfolded, the technologies that made them possible, and asks: where is this all heading next? The session will challenge practitioners to think critically about preparedness, resilience, and the limits of traditional cyber defenses in a world where attackers are innovating faster than ever.
16:15-16:45 (GMT +1)
Josephine Wolff
Professor of Cybersecurity Policy
Tufts University
From deepfakes to AI-generated fraud and even erroneous legal citations, the risks of artificial intelligence are no longer theoretical, they’re already here. This session will explore how AI failures are beginning to play out in real-world incidents and what early claims tell us about the exposures insurers must prepare for. We’ll examine the tricky question of where these claims land – cyber, D&O, E&O – and whether coverage is silent, affirmative, or excluded.
Attendees will also gain insight into how underwriters are (or aren’t) pricing AI risk amid limited loss history and evolving regulation, and whether standalone AI coverage is the next frontier. Expect a frank discussion of coverage gaps, underwriting challenges, and the urgent need to adapt policies to address AI-driven risks head-on.
Josephine Wolff, professor of cybersecurity policy at Tufts University, is a leading voice and educator on liability, cyber insurance, and the economics of information security. She brings razor-sharp, objective analysis and clear-eyed perspective to one of the most pressing issues facing the market today.
16:50-17:20 (GMT +1)
Patrick Milnamow
Senior Manager, Forensics Insurance & Federal Claims Services
Ernst & Young LLP
From grounded planes to empty shelves, 2026 could be the year when cyber risk reshapes entire industries. In aviation, a 400% surge in GPS spoofing incidents and a headline-making Qantas breach highlight how digital threats can jeopardize safety and trust.
In retail, cascading supply chain attacks on household names like M&S and Harrods expose how a single weak link can ripple into massive business interruption losses. And in healthcare, the stakes are uniquely high: organizations safeguard the most sensitive personal data, yet face ransomware, supply chain vulnerabilities, and growing risks tied to AI adoption. These attacks threaten not only financial stability but also patient safety and public trust.
Patrick Milnamow has deep experience guiding clients through complex cyber claims and business interruption losses. His perspective combines financial rigor with frontline insurance insight, making him the ideal voice to spotlight where the next big shocks may come from – and how the market can prepare.
17:25-17:55 (GMT +1)
We’ll wrap up the bootcamp by bringing all our speakers back together for an interactive panel that blends audience-driven Q&A with a sharp technical overview of the cyber insurance market.
After tackling standout questions submitted by attendees, the panel will dive into the biggest issues shaping the year ahead: how policies can adapt to emerging risks like automated vehicles, crypto, and sector-specific vulnerabilities; whether the future lies in one-size-fits-all coverage or tailored industry solutions; and how social engineering – supercharged by deepfakes and groups like Scattered Spider – continues to fuel some of the most high-profile attacks on insurers, airlines, and retailers.
The discussion will close with a forward-looking take on attack method trends and the evolution of key security controls. Expect a frank, expert-led conversation that connects technical realities with insurance market readiness.
The Cyber Insurance Bootcamp is designed to be concise enough for whole teams to join together – just set aside an afternoon (or morning, depending on your time zone) and complete the program in one sitting.
Contact us directly to arrange group access at support@cyberinsuranceacademy.com.
We also offer optional follow-up workshops and interactive exercises tailored to your team’s focus – whether underwriting, claims, or client advisory. These can be scheduled after the bootcamp to continue the learning in your own context.
If you’re planning to sign up your team or want to arrange a private workshop, please email support@cyberinsuranceacademy.com and our team will handle everything for you.
The bootcamp will take place on 11 November from 15:00–18:00 (UK time).
This is a fully online event – you can join from anywhere, no travel required.
Yes. The entire bootcamp will be recorded, and recordings will be made available to Premium Members. However, we strongly recommend attending live to take part in the Q&A and panel discussion.
The bootcamp runs for 3 hours, including short breaks between sessions.
Brokers, underwriters, claims professionals, and anyone working in or alongside cyber insurance who wants a concentrated, technical update on the risks and coverage debates shaping 2026.
Yes. The bootcamp is designed to be concise enough that teams can set aside an afternoon (or morning, depending on your time zone) and complete the training together in one sitting.
For companies looking to go deeper, we can also arrange follow-up workshops or interactive exercises to build on the bootcamp and address specific team or sector challenges.
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Demonstrates the quality of the learning of the Cyber Insurance Academy and confirms that it meets CII/ Personal Finance Society member CPD scheme requirements.
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