Underwriting & AI
Insights on how AI and machine learning are transforming cyber insurance underwriting, risk assessment, and policy decisions.
AI
AI in Cyber Underwriting: Attacker, Defender, and Underwriter Perspectives
Exploring how AI transforms cyber risk from three angles: how threat actors weaponize it, how security teams deploy it, and how underwriters must adapt their approach.
Michael Guiao
7 min read
Cyber Insurance · · 5 min read
Your Policy Says Cyber Event — But What Risk Does That Actually Expose?
Most cyber insurance policies define 'cyber event' so broadly that the term becomes meaningless for underwriting. Here is why that one definition matters more than any exclusion clause.
Newsletter · · 5 min read
Introducing The Underwriter's Edge
A new weekly newsletter for cyber underwriters, risk engineers, and brokers who want to stay ahead of threats, regulations, and emerging risks.
Underwriting · · 8 min read
The LOTL 2.0 Underwriting Playbook: Risk Selection Criteria When the Attacker Is an Algorithm
Practical underwriting framework for assessing cyber risk in the era of autonomous LOTL attacks. Includes revised risk scoring matrices, control weight adjustments, and application question updates for underwriters.
NIS 2 · · 10 min read
The NIS2 Audit Crunch: What Underwriters Need to Know Before June 30, 2026
With the June 30, 2026 NIS2 compliance audit deadline approaching, cyber underwriters face a narrow window to reassess risk profiles across their entire European portfolio. Here is what the audit requirement means for how you evaluate, price, and write cyber coverage.
NIS 2 · · 6 min read
NIS2 Compliance Checklist for 2026: What Brokers Need to Verify Before Coverage Placement
Before placing cyber coverage for NIS2 in-scope clients, verify these 10 compliance checkpoints. Missing documentation is the most common coverage gap.
Cyber Risk · · 2 min read
NIS2 and DORA: What Cyber Underwriters Need to Know
A practical breakdown of how the NIS2 Directive and DORA regulation affect cyber insurance underwriting in Europe.
NIS 2 · · 16 min read
NIS2 Underwriting Questions: What Every Cyber Insurance Broker Should Ask
Practical Line 1, Line 2, and Line 3 underwriting questions for NIS2-exposed clients. Essential vs important entities. Coverage gaps brokers should flag.
Underwriting · · 5 min read
Pricing Blind: When You Can't See the Risk You're Insuring
Cyber underwriters are pricing policies based on questionnaires and self-reported data while the real attack surface stays hidden. Here is what you are missing and how to fix it.
Ransomware · · 6 min read
Ransomware Underwriting Models in 2026: From Flat Premiums to Dynamic Risk Pricing
Cyber underwriters still using flat ransomware pricing are leaving money on the table. Here is how leading insurers are building dynamic pricing models using threat intelligence, sector exposure, and real-time data.
blog.featured
The Resilience Stack™: A Five-Layer Framework for Cyber Insurance Risk Assessment
Resilience Stack ·
12 min read
The Cyber Insurance Submission Crisis: 7 Reasons Brokers Can't Afford Manual Risk Assessments in 2026
Cyber Insurance ·
6 min read
Cyber Risk Quantification Tools 2026: The $50K Gap Between Free and Enterprise
Cyber Risk Quantification ·
4 min read
NIS2 Compliance Is Now an Underwriting Requirement — Every Broker's Duty of Care
NIS 2 ·
4 min read
Premium Report
2026 Cyber Risk Landscape Report
24 pages of threat analysis, claims data, and underwriting implications for European cyber insurance.
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