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AI Agents
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.
Michael Guiao
9 min read
AI · · 7 min read
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.
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.
Ransomware · · 7 min read
Ransomware Attack Vectors in 2026: What Risk Managers Must Monitor
Ransomware groups have moved beyond phishing. Here are the five dominant attack vectors risk managers need to understand — and how each one changes the insurance equation.
Cyber Risk · · 4 min read
The Uncomfortable Truth About Cyber Risk in 2026
Five things I'm seeing in the threat landscape that most security leaders aren't talking about enough.
Threat Intel · · 5 min read
Weekly Threat Digest: Week 19, 2026
Week 19 threat digest: 179 threats tracked, 24 critical, 142 high severity. Analysis for cyber insurance professionals.
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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