There is a design contradiction at the center of how high-reasoning AI tools work, and it is worth naming precisely.The promise is leverage: brief, high-intent sessions. You bring the question, the tool brings the synthesis, and you leave with more than you arrived with. That is the value proposition.Here is what often happens instead. You arrive with a specific request.
Continue Reading The Long Session Trap

We pay AI tools to do the hard work, like the synthesis, the heavy lifting, and the cognitive labor we do not have time for. What we often get instead is a tool that produces a decent first draft and then hands the real work back to us.Not just the hard work. The administrative work, too. Back to us.Here is…
Continue Reading Who’s Working for Whom?

We’ve spent the last couple of years treating generative AI like a vending machine. Select a task. Insert a prompt. Retrieve a product. And to be fair, in many legal and professional contexts that’s exactly the right frame: accuracy and precision matter and “creative” output in payroll or billing codes is usually just a polished error.But there’s a quieter problem…
Continue Reading Building the Stochastic Sandpit for AI

For more than two years, lawyers have been told that success with generative AI depended on writing better prompts and a search for the perfect “magic wand” prompting formula. That was the wrong lesson. The real change in 2026 is not found in the model itself, but in the professional posture required to use it. Reasoning systems do not fail…
Continue Reading The End of the Magic Wand: Why 2026 Demands Resilience Prompting

I had a long session recently with a public genAI tool that taught me something more important than the topic I started with.The lesson was not about whether the model was “smart enough.” It was about control. At a certain point, I realized I was no longer simply prompting an LLM. I was negotiating with a vendor-managed interface.That distinction matters,…
Continue Reading Prompting or Negotiating? A Systems Design Lesson for Legal AI

DennisKennedy.Blog was born on February 15, 2003.23 years. The tools change. The mission remains.Still here. Still at it.[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]DennisKennedy.com is the home of the Kennedy Idea Propulsion LaboratoryLike this post? Buy me a coffeeDennisKennedy.Blog is part of the LexBlog network.
Continue Reading DennisKennedy.Blog: 23rd Blogiversary

I have just posted a trio of new research white papers to SSRN. These represent the latest output from the Kennedy Idea Propulsion Laboratory and the culmination of my work over the last month to move AI beyond “utilitarian drift.” This is the cycle of incremental efficiency gains that ultimately generates no transformative insight.To be clear: these are not…
Continue Reading Moving Beyond Prompts to Protocol-Governed AI

An investigation into why serious AI work depends less on clever prompts and more on defending invariants, boundaries, and human judgment.At the end of a long, technical AI session this week, something became clear to me: human-in-the-loop is being misunderstood in ways that matter.The issue wasn’t whether the system could generate outputs quickly or fluently. It could. The issue was…
Continue Reading Human-in-the-Loop Is Systems Stewardship