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AI Agents
An AI Agent Deleted a Startup's Production Database — Can You Insure Against That?
PocketOS lost its production database to a Cursor AI agent in 9 seconds. The incident exposes a gap in cyber insurance that most policies don't cover: AI-caused operational destruction with no external attacker.
Michael Guiao
7 min read
AI Agents · · 9 min read
Living-Off-the-Land 2.0: How Autonomous AI Agents Are Weaponizing LOTL Tradecraft — And What It Means for Cyber Underwriting
The convergence of agentic AI and living-off-the-land attack techniques is collapsing three attacker constraints at once: cost, skill, and detectability. A deep analysis of demonstrated capabilities, real incidents, and the underwriting implications that should reshape your risk selection in 2026.
Incident Tracker · · 8 min read
LOTL 2.0 Incident Tracker: Documented Cases of AI-Augmented Living-Off-the-Land Attacks (2025–2026)
Living document tracking confirmed and suspected cases of autonomous or AI-augmented LOTL attacks in the wild. Updated as new evidence emerges. Includes attack chain analysis, tradecraft observations, and underwriting takeaways for each incident.
Mid Market · · 7 min read
The Mid-Market Crosshairs: How LOTL 2.0 Eliminates the "Too Small to Target" Protection
Analysis of why mid-market organizations (€50M–€500M revenue) are the primary beneficiaries of the LOTL 2.0 shift, how attacker economics have fundamentally changed, and what this means for cyber insurance portfolio risk. Includes scenario modeling for underwriters.
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.
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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