Artificial Intelligence

You Can’t Count on Prompting Your Way Out of AI Dysfunction

[Revised on 11 September 2025 to change the title and the text. The original title was If AI Gets One Thing Wrong, It Might Get Other Stuff Wrong.] Recently I saw on LinkedIn, in this post by Kara Dowdall, the following assessment of a contract: This assessment was generated by artificial intelligence. Or more specifically, by Claude, from Anthropic. I … Read More

ChatGPT Does “A Manual of Style for Contract Drafting”

At the recent ACC annual meeting, Adrian Goss—whom I first met a dozen years ago on a trip to Australia—told me he had uploaded some miscellaneous-provisions stuff from Practical Law and asked ChatGPT to redraft it so it complies with the guidelines in A Manual of Style for Contract Drafting. In this 2023 blog post, I discuss the notion of … Read More

Questionable Drafting in a Generative-AI Redline

I’ve written previously about conceptual shortcomings in relying on generative artificial intelligence to mark changes in the other side’s draft, commonly known as “redlining” (see this blog post and this blog post). Now, let’s look at a more basic problem: erratic drafting choices. This post is about one example of that. Recently the contract-lifecycle-management vendor Agiloft released (to quote this … Read More