Author: Kayne

On April 30, 2025, Clearlake Capital finalized a majority investment in Modernizing Medicine (“ModMed”), valuing the specialty healthcare software-as-a-service (SaaS) company at $5.3 billion. Ten weeks later, on July 9, an unauthorized party accessed two servers inside ModMed’s infrastructure. These weren’t production systems powering the electronic health records (EHR) used by 40,000 providers. They were…

Somewhere in Texas there’s a boardroom that wishes it had checked its meeting software settings. On August 28, 2026, Vice Chancellor Lori Will of the Delaware Court of Chancery (my favorite Court of Chancery!) ended a proxy fight at Empery Digital, a Bitcoin treasury company headquartered in Texas, by ruling that its board had no…

It’s sitting in a shared drive somewhere right now, gathering digital dust. Fourteen pages of well-researched risk analysis, a defensible budget request, and a routing slip with three approvals already collected. The fourth signature never came, and nobody can tell you exactly why. That’s the part nobody puts in the case study, because the honest…

When someone steals personnel files on 7,478 current and former employees, the invoice doesn’t arrive all at once. It dribbles in over two and a half years, disguised as legal fees, settlement payouts, credit monitoring subscriptions, and administrator invoices. Safe Fleet Holdings, the Missouri-based fleet safety manufacturer that Oak Hill Capital sold to Clarience Technologies…

Perplexity AI secured a unanimous appellate victory this summer, but about seven weeks later, Amazon filed a First Amended Complaint accusing Perplexity of lying about how its agent works. The Ninth Circuit had vacated Amazon’s preliminary injunction and told the lower court that agentic software acts as a tool for users, not an independent actor…

Picture applying to more than 100 jobs through the same screening platform and never landing a single interview. The vendor calls it an algorithmic anomaly. A federal judge in California saw a viable discrimination claim. On June 26, 2026, Judge Rita Lin denied Workday’s motion to dismiss in Mobley v. Workday Inc.. Fair Employment and…

A recent discovery ruling in Colorado is the clearest argument I’ve seen for why restrictive AI policies fail, and what to do instead. On August 31, 2026, a magistrate judge in Colorado resolved a routine-looking discovery fight and, in doing so, handed corporate America a free lesson in AI governance. The case was Dunn v….

There’s a conversation happening in boardrooms where cybersecurity doesn’t have a seat at the table. Risk registers track credit exposure, supply chain concentration, and litigation, while security findings circulate in a parallel universe of vulnerability counts and CVSS scores that no CFO can price. The consequence is that every security decision, funded or deferred, becomes…

There’s a settlement hiding in the public record that cost American Consumer Credit Counseling as much as two million dollars, and not a single tech blog covered it. The silence isn’t a conspiracy; nobody watched the Massachusetts Superior Court docket for case number 2581CV02933; part of that might be because their website’s not the friendliest….

In 2021, Krafton, the South Korean publisher behind PlayerUnknown’s Battlegrounds (PUBG), bought the game studio Unknown Worlds for $500 million. The deal promised the studio’s leadership another $250 million if they hit their revenue targets through December 2025, and it made firing them hard. “Cause” meant a felony, gross misconduct, leaking confidential information, or intentional…

Archer Daniels Midland is mostly out of the False Claims Act woods, and the story of how it got there is the most useful ruling on cyber-FCA enforcement in years. Nobody sued. Nobody settled. The relator, Mark Pannek, lost on paper, in a memorandum and order from Judge Sanjay Harjani of the Northern District of…

This week, two things happened involving the same federal document. On September 9, Washington Technology reported that the Cybersecurity Maturity Model Certification (CMMC) Phase 2 suspension had been “locked in with binding regulation,” a step change from a mere pause that would make reversal harder. The same week, the analysts at RedSpin compared the new…