Law librarian.
Former attorney.
Occasional toolmaker.
I teach legal research, writing, and technology. I write about what generative AI gets wrong in legal research. And I build small tools to teach with.
Writing
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- California Emerges as the Leader in Regulating Attorneys’ Use of Generative Artificial IntelligenceGuest Post: Jackie McCloud, Research and Instructional Services Librarian, Indiana University Robert H.
- Keeping Up With AI in the Law, Three Years LaterAn update to my 2023 post on keeping up with generative AI: what changed, the five sources I read now, people worth following, and why my best news comes from communities.
- Find Some Good Reads with My Textbook Explorer & Reading ListTwo resources for anyone teaching AI or legal tech: a textbook explorer with chapters tagged by topic, and my 21st Century Lawyering reading list, class by class.
- Six Questions and Three Tests Before You Adopt an AI ToolSix questions and three low-cost tests for deciding whether to adopt an AI tool, use by use, with a worksheet, vendor data-diligence questions, and a sample audition set.
Resources
All resources →- Books and teaching resources on AI in legal practiceTextbooks, casebooks, study aids, and open materials for teaching AI in legal practice, grouped by how students can get them.
- Sources for following AI and lawNewsletters, news sites, podcasts, video channels, blogs, trackers, and a feed reader for keeping up with AI, legal AI, and AI law and policy.
- 21st Century Lawyering: Spring 2026 reading listThe class-by-class readings for a law school course on legal technology and AI: LLM basics, prompting, legal design, ethics, hallucinations, research, vibe-coding, bias, agents, access to justice, and the business of law.
Projects
All projects →Teaching tools
- Citation Hallucination Game
Classroom exercise where students read a brief and decide, citation by citation, which cases are real and which were fabricated by an AI.
- Prompt Coach
Split-panel workspace: students chat with Claude on the left and get feedback on the prompt itself on the right, including a hallucination-risk review.
- Boolean Builder
Walks a researcher through building a terms-and-connectors search step by step. The "Effortless Boolean" tool from the blog.
Research tooling and side projects
- The Missing Link
Browser extension that finds the case an article mentioned but did not link, using Claude to identify it and CourtListener to fetch it.
- Citation Verifier
Checks AI-generated case citations against CourtListener: does the cite exist, does it belong to the case named, and does the case support the proposition it is cited for.
- Docket Q&A
Ask questions of bankruptcy case documents pulled from the RECAP Archive.
Just for fun
- Bug Lab
Creature-mixing ecosystem game: splice bug genes and release hybrids into a procedurally generated world.
- Potato Simulator
A brave potato battles evil kitchen utensils across eight levels. Single HTML file, HTML5 canvas.
- Draw-o-matic
Arcade-style drawing prompt generator with zero-repeat memory and a creepy-cute streak.