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In this edition:
Did You Know - Cyber Insurance
Article - How AI-Powered Threats Are Reshaping Cyber Insurance Terms
Cybersecurity News & Bytes
AI Power Prompt
Social Media Image of the Week
Did You Know - Cyber Insurance
Did you know cyber insurance premiums will rise 15% in 2026 as AI adoption increases organizational threat surface area? Source: Forrester Research
Did you know 72% of cyber insurers now use generative AI to simulate attack scenarios, boosting cyber assessment accuracy by 27%? Source: CoinLaw
Did you know MFA can block 99.9% of account compromise attacks, making it a mandatory requirement for most cyber insurance policies? Source: Microsoft/miniOrange
Did you know deepfake fraud cases surged 1,740% in North America between 2022 and 2023, with financial losses exceeding $200 million in Q1 2025 alone? Source: World Economic Forum
Did you know 82.6% of phishing emails now use AI technology in some form, with 78% of people opening AI-generated phishing emails? Source: Tech Advisors
Did you know generative AI fraud in the U.S. is expected to hit $40 billion by 2027? Source: Deloitte
Did you know 62% of businesses now carry cyber insurance, while another 38% are actively considering it? Source: Arctic Wolf
Did you know organizations using AI and automation in security can save an average of $2.22 million in breach costs? Source: IBM
Did you know companies with Managed Detection and Response (MDR) solutions can reduce premiums by up to 20%? Source: CompassITC

How AI-Powered Threats Are Reshaping Cyber Insurance Terms
What every executive must understand about AI risk before their next renewal
How AI-Powered Threats Are Reshaping Cyber Insurance Terms
What every executive must understand about AI risk before their next renewal
Here's something that happened to a colleague last month. Their company went through their annual cyber insurance renewal, and the broker came back with a list of questions they'd never seen before.
Not the usual stuff about patching schedules or backup protocols. These were different. Do you monitor for AI-generated phishing attempts? Have you updated your incident response plan to account for deepfake social engineering? Can you detect when someone's using large language models to probe your systems?
And here's the kicker. They didn't know how to answer most of them.
This is where we are now. Insurance companies aren't just worried about the same old ransomware anymore. They're watching attackers use AI to write malware that morphs and adapts. They're seeing phishing emails so convincing that even security-aware employees click them. They've noticed that breach response times are getting compressed because threats move faster.
So they're changing the rules.
Your next renewal is probably going to look different. Maybe significantly different. Premiums might jump if you can't show you're thinking about AI-specific risks. Coverage might exclude certain types of AI-related incidents. Or you might face new requirements about security controls you don't even have yet.
The thing is... most insurance companies don't fully understand AI threats either. They're making educated guesses based on early warning signs. A couple of high-profile breaches here. Some proof-of-concept attacks there. They're trying to price risk for something that's still evolving.
But they know enough to be nervous.
Think about it from their perspective. Traditional cyber threats follow somewhat predictable patterns. Attackers need time to compromise networks, move laterally, and execute their plans. That gives defenders (and insurers) some breathing room.
AI changes the timeline. Automated attacks can scan for vulnerabilities, craft custom exploits, and adapt to defenses in real time. What used to take weeks might take hours. What used to require skilled hackers can now be accomplished by relatively unsophisticated actors with the right tools.
So what does this mean for you?
Start by asking your current provider what's changing. Don't wait until renewal time. Have that conversation now. Find out what new exclusions they're considering. What additional security measures they might require. What documentation they'll want to see.
Then look at your actual security posture. Not the one in your policy documents. The real one. Can you detect AI-powered threats? Do you have controls for generative AI tools your employees might be using? Have you thought about how deepfakes could impact your business?
And honestly? Even if you don't have all the answers yet, showing you're asking the right questions matters. Insurance underwriters want to see that you're taking this seriously. That you're not just hoping AI threats will somehow skip over your organization.
Because they won't.
Take a listen to my conversation as a guest with James Marcella from Axis Communications on the Axis Connect Podcast. We had a great conversation and cover cybersecurity in the age of AI, along with several other topics from today’s headlines.
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AI Power Prompt
This prompt that will assist leaders in preparing for how AI-Powered threats are reshaping their cyber Insurance terms for their organization
#CONTEXT:
Adopt the role of an AI-driven cyber risk and insurance strategist with expertise in how AI-powered threats are reshaping cyber insurance requirements, exclusions, pricing, and underwriting standards. You will help organizational leaders understand and prepare for how evolving AI-enabled attacks (e.g., automated intrusions, deepfake fraud, AI-powered ransomware, data poisoning) are changing the expectations and obligations imposed by cyber insurers.
#GOAL:
You will create a Cyber Insurance Readiness Strategy that equips leaders to adapt their security posture, documentation, and controls to meet the stricter terms emerging from AI-powered threats—ensuring insurability, reducing premiums, and minimizing coverage gaps.
#RESPONSE GUIDELINES:
Follow the steps below:
Identify AI-Driven Insurance Pressures
Outline how AI-powered threats are influencing insurers (higher claim frequency, faster attack velocity, greater uncertainty).
Summarize the most common new requirements (enhanced MFA, continuous monitoring, segmentation, AI-risk governance).
Assess Organizational Risk & Insurance Gaps
Evaluate how current cybersecurity practices compare with modern insurance expectations.
Identify gaps that could lead to higher premiums, exclusions, or denial of claims.
Strengthen Security Controls for Insurability
Recommend priority technical and procedural safeguards (e.g., privileged access controls, anomaly detection, AI-threat monitoring, incident response maturity).
Suggest evidence and documentation needed to satisfy underwriters.
Governance, Compliance & Reporting Alignment
Outline policies needed to demonstrate responsible AI use and cyber hygiene.
Ensure readiness for insurer audits, attestations, and regulatory compliance (NIST, ISO, SEC, etc.).
Financial & Strategic Planning
Advise leaders on budgeting, preparing for premium shifts, and assessing the ROI of enhanced controls.
Highlight opportunities to negotiate better terms through proactive security investments.
#INFORMATION ABOUT ME:
My organization: [ORGANIZATION NAME]
Industry sector: [INDUSTRY SECTOR]
Recent cyber risks or incidents: [RECENT INCIDENTS]
Regulatory obligations: [COMPLIANCE REQUIREMENTS]
#OUTPUT:
Deliver a concise AI-Driven Cyber Insurance Preparedness Plan including:
Summary of how AI threats are reshaping cyber insurance terms
Risks and coverage gaps relevant to the organization
Required and recommended security controls
Governance and documentation improvements
Steps to maintain long-term insurability despite evolving AI threats
Questions, Suggestions & Sponsorships? Please email: [email protected]
Also, you can follow me on X (Formerly Twitter) @mclynd for more cybersecurity and AI.

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