ARTICLE
17 October 2025

Turing's Ambiguity – Squaring AI Convenience With Human Expectations In Transactional Settings

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Wordy title, right? Well, if you've ever received an AI-generated email highlighting deal points that reads more like a dissertation on economics...
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Wordy title, right? Well, if you've ever received an AI-generated email highlighting deal points that reads more like a dissertation on economics, you might see how the title matches the ever-evolving technological environment of our day-to-day lives.

Developed by Alan Turing in 1949, the Turing Test is a test of a machine's ability to demonstrate intelligent human behavior and a human participant's ability to identify what's exhibited by a machine or a human. Ex Machina portrayed the cultural risks and dilemmas central to the heart of Turing in a very good, but disturbing movie a few years ago. And while I'm not dealing with the competing motives of a tech trillionaire and artificial super intelligence that afflicted the characters in that story, I am seeing the use and greater influence of artificial intelligence ("AI") more in every facet of the transactional environment.

Don't get me wrong – I'm neither a Luddite nor indifferent to the benefits of AI tools like ChatGPT, Claude, Google Gemini, and many others. Success in any business effort requires efficiency, and AI offers an avenue for optimizing efficiency we haven't seen since probably the introduction of the printing press. I only aim to offer caution to the unrestrained reliance on such tools that can lead to outcomes that diverge—whether partially or completely—from the intentions of their users, especially in transactions.

I haven't taken an official Turing Test, but lately I find myself in a quasi-test setting almost weekly. New matters involve new doc sets, and new doc sets occasionally include some form of a contract or terms generated by AI. Sometimes it's a quick and tidy approach to addressing a straightforward transaction. Other times it's a labyrinth of terms and conditions that need to be unwound and restructured to fit the parties' LOI or general intentions. This experience is by no means limited to M&A. I've seen it in real estate, corporate and entity governance, and general transactional matters.

Fortunately, so far, those latter situations haven't involved a signed instrument between the parties. If and when that happens though, disputes and issues on a contract's interpretation and enforcement remain governed by the plain language of the agreement. At that point, the concern becomes what exposure a party has under the contract's terms and conditions and the extent of that exposure. And that Turing's ambiguity. . . well, it's not altogether unlikely that ambiguous terms in a contract are interpreted and enforced in opposition to not only a party's original intent for a transaction, but also its best interest.

The content of this article is intended to provide a general guide to the subject matter. Specialist advice should be sought about your specific circumstances.

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