Most policyholders purchasing directors and officers (D&O) liability insurance never contemplate the possibility that their insurer will one day demand repayment of advanced defense costs, let alone seek interest on top of repayment.  Although many D&O policies preserve an insurer’s contractual right to seek reimbursement of defense costs that are ultimately determined not to be…

Policyholders increasingly turn to artificial intelligence (“AI”) platforms to answer insurance coverage questions.  This is risky because: (1) AI models hallucinate legal content at alarming rates; and (2) AI cannot apply nuanced, fact-specific and jurisdiction-specific legal analysis.  As OpenAI Foundation recently acknowledged, “ChatGPT . . . neither has nor uses any degree of legal knowledge…

When private equity fund managers think about insurance, they usually think of Representations & Warranties Insurance (“RWI”).  That makes sense—RWI covers representations baked into the deal itself that are front of mind when buying and selling portfolio companies (“PortCos”).  But once a deal closes and a PortCo continues operations under new PE ownership, a whole…

On June 29, 2026, Virginia’s $207 billion budget bill became law, bringing a retail cannabis framework that authorizes licensed sales beginning July 1, 2027.  Businesses entering this market should be prepared for unique insurance challenges, as no Virginia court has yet interpreted how standard commercial policies apply to such businesses.…

PART 1: Representations & Warranties Insurance in Today’s Deal Market: Why It Matters More Than Ever

Introduction

Representations and warranties insurance (“RWI”) has rapidly evolved from a niche product used in select transactions to a near-standard feature in middle-market private equity deals. What was once viewed as an optional risk-transfer tool is now often a…

Employers nationwide are experiencing a new wave of ERISA litigation targeting so-called “tobacco surcharges” on employees enrolled in employer-sponsored health plans. Because these lawsuits are generally brought as putative class actions, the stakes can be significant and some multi-million dollar settlements have already become public. But employers need not face the costs of defending and…

The insurance industry has been swift to adopt artificial intelligence (“AI”). According to consulting firm McKinsey & Company, 76% of insurers surveyed have already begun using generative AI in their day-to-day operations. [1] This adoption spans the different facets of insurers’ work cycles, including claims, underwriting, legal, and risk management. Policyholders and their attorneys must…