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David S. Kemp
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Learning Machines


Lawyers are learning to work with artificial intelligence. Artificial intelligence is learning to work with law. This blog explores how — through pedagogy, practice, policy, and the ethical questions that connect them.

  • What Your AI Forgets Mid-Sentence — And What to Do About It

    March 29, 2026 AI Legal Technology Prompt Engineering

    LLMs degrade predictably as their context windows fill — losing track of middle-document content, dropping earlier conversation history, and producing confident output built on incomplete inputs. For lawyers using these tools on long documents, the question is not whether it happens but how to structure your work to prevent it.

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  • You Probably Have a Duty to Warn Your Clients About ChatGPT

    March 27, 2026 AI Legal Ethics Attorney-Client Privilege

    Heppner established that consumer AI conversations are not privileged. But the case also raises an uncomfortable question for practicing lawyers: if a known hazard to the privilege now exists, do you have a duty to warn your clients about it? The answer, under existing ethics rules, is almost certainly yes.

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  • The API Is Not a Compliance Strategy

    March 23, 2026 AI Data Privacy Compliance

    Using an LLM through an API rather than a consumer chatbot improves your data-handling posture — sometimes dramatically. But an API alone does not satisfy FERPA, HIPAA, or any other regulatory framework, and treating it as though it does mistakes a technical control for a legal one.

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  • Your AI Conversations Are Not Confidential — And a Federal Court Just Said So

    March 20, 2026 AI Legal Ethics Data Privacy

    A comparison of Anthropic's data-handling policies across Claude's consumer and commercial tiers — and why the distinction now carries real legal consequences after the SDNY's decision in United States v. Heppner.

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© 2026 David S. Kemp.

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The views expressed on this blog are the author's own and do not represent those of any employer, institution, or affiliate. Nothing here constitutes legal advice. The author uses Claude Opus to assist with website and blog design and content.