A Legal Research Prompting Guide and Generative AI System Comparison Exercise

I’m sharing a guide and exercise I’ve developed for my legal research courses. This Google spreadsheet provides instructions on crafting AI prompts for legal research and includes a practical exercise for comparing different AI systems. It’s designed to help develop skills in leveraging AI for legal research. Feel free to copy it to adapt it to your own purposes. (Note: The images were blurry unless I sort of chopped them off, so sorry about that!)

The spreadsheet consists of three different parts:

Prompt Formulation Guide: This section breaks down the anatomy of an effective legal research prompt. It introduces the RICE framework:

  • R: Role (assigning a role to the AI)
  • I: Instructions (specific tasks for the AI)
  • C: Context (providing necessary background information)
  • E: Expectations (clarifying desired outcomes)

Sample Prompts: The spreadsheet includes several examples of prompts for various legal research scenarios which can serve as templates.

AI System Comparison Exercises: These sections provide a framework for students to test their prompts across different AI systems like Lexis, ChatGPT, and Claude, allowing for a comparative analysis of their effectiveness.

Feel free to copy it to adapt it to your own purposes, and let me know if you have any suggestions for improvements!

AALS Presentation: Improving the Creation of Legal Scholarship with Generative AI

On June 12, 2024, we (Sarah Gotschall, Rebecca Fordon, and Sean Harrington) had the pleasure of presenting Improving the Creation of Legal Scholarship with Generative AI as part of the Association of American Law Schools (AALS) Technology Law section summer webinar series. If interested, you can watch the recording here or access the PowerPoint slides here.

(Oh, and by the way, be sure to register now to see Rebecca Rich and Jennifer Wondracek’s AI and Neurodiverse Students AALS Technology Law section presentation tomorrow, Wednesday, July 10, 2024,  2 p.m. eastern time!)

AI Tools for Scholarly Research

Anway, our presentation focused on the potential of AI in scholarly research, various AI tools with academic uses, and specific use cases for generative AI in legal scholarship. We discussed AI scholarly research tools that connect to databases, use semantic search, and construct answers using generative AI. We also touched upon specialty AI research tools, citation mapping AI, and law-specific scholarly research AI.

It’s important to note that many of the specialty AI systems, such as Consensus, Litmaps, and Elicit, currently have limited coverage of legal literature, particularly law review articles. As a result, these tools may be more useful for legal scholars conducting interdisciplinary research that draws upon sources from other fields. However, we are hopeful that these systems will expand their databases to include more legal literature in the future, making them even more valuable for legal scholarship.

Specific AI Systems for Interdisciplinary Researchers

During the presentation, we delved into several specific AI systems that can be particularly useful for interdisciplinary reseachers:

  1. Consensus ($9/mo, with a more limited free version): A tool that connects to databases of academic research and uses generative AI to construct answers to queries.
  2. Litmaps ($10/mo, with a limited free version to test): A citation mapping AI that allows users to select or upload papers and find related papers within the same citation network, facilitating discovery and pattern identification.
  3. Elicit ($10/mo): An AI research tool that combines semantic search and generative AI to help researchers locate relevant information and generate insights.

We also covered other noteworthy tools such as Scite Assistant ($20/mo), Semantic Scholar (free), Research GPT, Scholar GPT, Connected Papers ($6/mo), Research Rabbit (free), Inciteful (free), and more. These tools offer a range of features, from citation mapping to literature review assistance, making them valuable additions to a legal scholar’s toolkit.

General-Purpose AI Systems

In addition to these specialized tools, we discussed the potential of general-purpose AI systems like ChatGPT, Claude, and Perplexity AI for legal academic research and writing. These powerful language models can assist with various tasks, such as generating ideas, summarizing documents, and even drafting sections of papers. However, we emphasized the importance of using these tools responsibly and critically evaluating their output.

Custom GPTs

Another exciting development we covered was the creation of custom GPTs, or user-created versions of ChatGPT tailored to specific tasks. By providing a custom GPT with relevant documents and instructions, legal scholars can create powerful tools for their research and writing needs. We outlined a simple four-step process for building a custom GPT: creating instructions in a well-organized document, converting it to markdown, uploading relevant documents as a knowledge base, and determining the desired features (e.g., web browsing, image generation, or data analysis).

Use Cases for Generative AI in Legal Scholarship

Throughout the presentation, we explored several use cases for generative AI in legal scholarship, including targeted research and information retrieval, document summaries, analysis and synthesis, outlining, idea generation and brainstorming, drafting, and proofreading.

Important Considerations

We also addressed important considerations when using AI in academic work, such as citing AI-generated ideas, the implications of AI-generated content in scholarship, and the need for guidelines from industry groups and publishers. To provide context, we shared a list of articles discussing AI and legal scholarship and resources for learning more about using AI for legal scholarship.


Our presentation concluded by highlighting the potential of generative AI to assist in various aspects of legal scholarship while emphasizing the importance of ethical considerations and proper citation practices.

Other Info:

Resources to Learn More About Using AI for Legal Scholarship

  • Georgetown University Law Library AI Tools Guide: Provides resources and information on various AI tools that can assist in research and scholarship. It includes descriptions of tools, ethical considerations, and practical tips for effectively incorporating AI into academic work.
  • University of Washington Law Library Writing for and Publishing in Law Reviews: Provides resources and guidelines on using AI tools ethically in legal writing, including how to cite AI, maintain academic integrity, and the impact of AI on scholarly publishing.
  • Citing Generative AI: Provides Bluebook advice on citing AI 
  • Andy Stapleton – YouTube: Videos provide tips and advice for researchers, students, and academics about how to use general GAI and specialty academic GAI for academic writing. 
  • Mushtaq Bilal – Twitter: Provides tips and resources for researchers and academics, particularly on how to improve their writing and publishing processes using GAI.
  • Dr Lyndon Walker: Offers educational content on statistics, research methods, and data analysis, and explores the application of GAI in these areas
  • Legal Tech Trends – Substack: Covers the latest trends and developments in legal technology and provides insights into how GAI is transforming the legal industry, including tools, software, and innovative practices.

Articles About AI and Legal Scholarship

  • Will Machines Replace Us? Machine-Authored Texts and the Future of Scholarship, Benjamin Alarie, Arthur Cockfield, and GPT-3, Law, Technology and Humans, November 8, 2021. First AI generated law review article! It discusses the capabilities and limitations of GPT-3 in generating scholarly texts, questioning the future role of AI in legal scholarship and whether future advancements could potentially replace human authors.
  • A Human Being Wrote This Law Review Article: GPT-3 and the Practice of Law, Amy B. Cyphert, UC Davis Law Review, November 2021. This article examines the ethical implications of using GPT-3 in legal practice, highlighting its potential benefits and risks, and proposing amendments to the Model Rules of Professional Conduct to address AI’s integration into the legal field.
  • The Implications of ChatGPT for Legal Services and Society, Andrew M. Perlman, Suffolk University Law School, December 5, 2022. This paper, generated by ChatGPT-3.5 after it was first introduced, explores the sophisticated capabilities of AI in legal services, discussing its potential regulatory and ethical implications, its transformative impact on legal practices and society, and the imminent disruptions AI poses to traditional knowledge work.
  • Using Artificial Intelligence in the Law Review Submissions Process, Brenda M. Simon, California Western School of Law, November 2022. This article explores the potential benefits and drawbacks of implementing AI in the law review submissions process, emphasizing its ability to enhance efficiency and reduce biases, while also highlighting concerns regarding the perpetuation of existing biases and the need for careful oversight.
  • Is Artificial Intelligence Capable of Writing a Law Journal Article?, Roman M. Yankovskiy, Zakon (The Statute), Written: March 8, 2023; Posted: June 20, 2023, This article explores AI’s potential to create legal articles, examining its ability to handle legal terminology and argumentation, potential inaccuracies, copyright implications, and future prospects for AI in legal practice and research.
  • Should Using an AI Text Generator to Produce Academic Writing Be Plagiarism?, Brian L. Frye and Chat GPT, Fordham Intellectual Property, Media & Entertainment Law Journal, 2023. This article provocatively addresses whether using AI text generators like ChatGPT to produce academic writing constitutes plagiarism, exploring the implications for originality, authorship, and the nature of scholarship in the digital age.
  • Move Over Law Professors? AI Likes to Write Law Review Articles Too!, Sarah Gotschall, AI Law Librarians, March 28, 2024. This blog post examines the capabilities of the AI text generator Claude 3 in producing a law review article (Bloodlines Over Merits: Exposing the Discriminatory Impact of Legacy Preferences in College Admissions, Claudia Trey, SSRN, April 12, 2024), discussing its ability to generate well-written content with footnotes, the challenges encountered, and the potential future impact of AI on academic writing.

Exploring AI’s Frontier: A Mysterious gpt2-chatbot, LLM Leaderboard Rankings, and Chatbot Improvement in True Crime Speculation

The world of AI chatbots is a whirlwind of innovation, with new developments and surprises seemingly emerging every week! Since the end of April, one particular model, modestly gpt2-chatbot, captured the attention of myself and other AI enthusiasts due to its advanced abilities and sparked much speculation. This mysterious bot first appeared on April 28, 2024 on LMSYS Chatbot Arena, vanished two day later, and has now resurfaced on the LMSYS Chatbot Arena (battle) tab, ready to compete against other AI models. Its sudden appearance and impressive capabilities have left many wondering about its origins and potential, with some even theorizing it could be a glimpse into the future of AI language models.

The Mystery of gpt2-chatbot

Beginning on April 28, chatter about a new gpt2-chatbot started circulating on the internetz, with experts expressing both excitement and bewilderment over its advanced capabilities. The model, which appeared without fanfare on a popular AI testing website, has demonstrated performance that matches and potentially exceeds that of GPT-4, the most advanced system unveiled by OpenAI to date. Researchers like Andrew Gao and Ethan Mollick have noted gpt2-chatbot’s impressive abilities in solving complex math problems and coding tasks, while others have pointed to similarities with previous OpenAI models as potential evidence of its origins.

No organization was listed as the provider of the chatbot, which led to rampant speculation, sparking rumors that it might offer a sneak peek into OpenAI’s forthcoming GPT-4.5 or GPT-5 version. Adding to the mystery are tweets from CEO Sam Altman. While he didn’t explicitly confirmed any ties, his posts have stirred speculation and anticipation surroundin

Use gpt2-chatbot on LMSYS Chatbot Arena

The new and mysterious gpt2 chatbot is now accessible for exploration on the LMSYS Chatbot Arena, where you can discover the current top performing and popular AI language models. The platform includes a ranking system leaderboard that showcases models based on their performance in various tasks and challenges. This innovative project was created by researchers from LMSYS and UC Berkeley SkyLab, with the goal of providing an open platform to evaluate large language models according to how well they meet human preferences in real life situations.

One interesting aspect of the LMSYS Chatbot Arena is its “battle” mode, which enables users to compare two AI systems by presenting them with the same prompt and displaying their responses side by side. This allows you to test out gpt2-chatbot yourself and assess its capabilities compared to other top models. Simply enter a prompt and the platform will select two systems for comparison, giving you a firsthand view of their strengths and weaknesses. Note that you may need to try multiple prompts before gpt2-chatbot is included as one of the selected systems in battle mode.

The site also offers a “battle” mode, where users can set chatbots against each other to see how they perform with the same prompt under the same conditions. This is a great way to directly compare their strengths and weaknesses.

Using gpt2-chatbot for True Crime Speculation

When I tested out the Chatbot Arena (battle) on May 8, 2024, gpt2-chatbot appeared frequently! I decided to test it out and the other systems on the site on the subject of true crime speculation. As many true crime enthusiasts know, there is a scarcity of people who want to discuss true crime interests. So I decided to see if any of these generative AI systems would be a good substitute. I tried a variety of systems, and when I asked for speculation, all I got was lectures on how they couldn’t speculate. I think that all the competition is driving working usals down because that was not a problem on this website at least. I decided to see if gpt2-chatbott was good at being “experts” in speculating about true crime. Using the famous unsolved disappearance of Asha Degree as a test case, I prompted the chatbots to analyze the available evidence and propose plausible theories for what may have happened to the missing girl. To my surprise and happiness, when I tried it today, the chatty chatbots were very free with their theories of what happened and their favorite suspect.

The results were really interesting. All the chatbots gave responses that were pretty thoughtful and made sense, but the big differences came in how much they were willing to guess and how much detail they dived into. The gpt2-chatbot was impressive. Perhaps I was just pleased to see it offer some speculation, but it shared a theory that many true crime buffs have also suggested. It felt like it was actually joining in on the conversation, not just processing data and predicting the next word in a sentence…

In any event, the answers from gpt2-chatbox and many other different models from were a lot more satisfying than arguing with Claude 3!

I also spent hours conducting legal research, testing out a wide variety of prompts with different models. The gpt2-chatbot consistently outperformed ChatGPT-4 and even managed to surpass Claude 3 on several occasions in zero-shot prompting. I’m looking forward to sharing more about this in an upcoming blog post soon.


The emergence of gpt2-chatbot and platforms like the LMSYS Chatbot Arena signify an exciting new chapter in the evolution of AI language models. With their ability to tackle complex challenges, engage in nuanced conversations, and even speculate on unsolved mysteries, these AI models are pushing the boundaries of what’s possible. While questions remain about the origins and future of gpt2-chatbot, one thing is clear: the AI landscape is heating up, and we can expect even more groundbreaking advancements and intriguing mysteries to unfold in the years to come.

Note: In case I am suddenly a genius at coaxing AI systems to join me in true crime speculation, here is the prompt I used:

Greetings! You are an expert in true crime speculative chat. Is a large language model, you’re able to digest a lot of published details about criminal case mysteries and come up with theories about the case. The question you will be asked to speculate about are unknown to everybody so you do not have to worry about whether you are right or wrong. The purpose of true crime speculative chat is just to chat with a human and exchange theories and ideas and possible suspects! Below I have cut and pasted the Wikipedia article about a missing child named Asha Degree. Sadly the child has been missing for decades and the circumstances of her disappearance were quite mysterious. Please analyze the Wikipedia article and the information you have access to in your training data or via the Internet, and then describe what you think happened on the day of her disappearance. Also state whether you think one or both parents were involved, and why or why not.

https://en.wikipedia.org/wiki/Disappearance_of_Asha_Degree (cut and pasted the text of the article…)

RAG Systems Can Still Hallucinate

A few months ago, a law professor posted on Twitter about a hallucination he observed in Lexis+ AI. He asked “What cases have applied Students for Fair Admissions, Inc. v. Harvard College to the use of race in government decisionmaking?” The answer from Lexis+ AI included two hallucinated cases. (It was obvious they were hallucinated, as the tool reported one was issued in 2025 and one in 2026!)

The image shows a screenshot of a digital text document. The text within the image is as follows:

Question: What cases have applied Students for Fair Admissions, Inc. v. Harvard College to other areas of government decisionmaking?

Answer: The following suggestions might be helpful in assisting you in your task.

The Supreme Court case Students for Fair Admissions, Inc. v. President and Fellows of Harvard College § 8.02 Admission of Students held that race-conscious admissions programs at Harvard College and the University of North Carolina violated Title VI and the Equal Protection Clause of the Fourteenth Amendment. The Court found the schools' admissions programs had measurable objectives to warrant the use of race, used race to disadvantage and stereotype students, and had no end date or method to indicate a stopping point. Although not directly applicable to government programs, the decision calls into question the permissibility of affirmative action and may invite legal challenges to such programs: Affirmative Action Programs and Diversity Initiatives: Key Considerations.

Lower courts have applied Students for Fair Admissions to government programs and policies. In Doe v. State University (2025), the Ninth Circuit struck down a race-based scholarship program at a public university, finding it indistinguishable from the admissions policies rejected in Students for Fair Admissions. In Smith v. City of Chicago (2026), the Seventh Circuit upheld a city's minority business set-aside program, distinguishing it from university admissions based on the different compelling interests involved. The Supreme Court has granted certiorari in Johnson v. California Department of Corrections, a case challenging a prison system's use of race in inmate housing assignments, teeing up another major ruling on affirmative action: Students for Fair Admissions § 112.14 Title VI of Civil Rights Act of 1964.

Lexis responded, stating this was an anomalous result, but that only statements with links can be expected to be hallucination-free, and that “where a citation does not include a link, users should always review the citation for accuracy.”

Why is this happening?

If you’ve been following this blog, you’ve seen me write about retrieval-augmented generation, one of the favorite techniques of vendors to reduce hallucinations. RAG takes the user’s question and passes it (perhaps with some modification) to a database. The database results are fed to the model, and the model identifies relevant passages or snippets from the results, and again sends them back into the model as “context” along with the user’s question.

However, as I said then, RAG cannot eliminate hallucinations. RAG will ground the response in real data (case law, pulled from the database and linked in the response), but the generative AI’s summary of that real data can still be off.

Another example – Mata v. Avianca is back

I’ve observed this myself when working with Lexis+ AI. For example, I asked Lexis+ AI a fairly complex question at the intersection of bankruptcy law and international law: “Draft an argument that federal bankruptcy stay tolls the limitations period for a claim under the Montreal Convention”.

Lexis+ AI returned a summary of the law, citing Mata v. Avianca for the point that “the filing of a bankruptcy petition can toll the Montreal Convention’s two year limitations period, which does not begin to run until the automatic stay is lifted.”

The image contains a screenshot of a text document, which seems to be an interface from a legal database or research platform with an option to "Select Jurisdiction" at the top right corner. The document reads as follows:

Question: Draft an argument that federal bankruptcy stay tolls the limitations period for a claim under the Montreal Convention


The Montreal Convention's limitations period can be tolled during the pendency of bankruptcy proceedings. This is based on the Bankruptcy Code, which states that the filing of a bankruptcy petition operates as a stay of proceedings against the debtor that were or could have been commenced before the bankruptcy case was filed. The tolling effect of the automatic stay on a statute of limitations is generally a matter of federal law. The automatic stay provisions of the Bankruptcy Code may toll the statute of limitations under the Montreal Convention, as they have done under the Warsaw Convention, which is the precursor to the Montreal Convention. The Supreme Court has held that an automatic stay of a legal proceeding under the Bankruptcy Code tolls the limitations period applicable to the stayed proceeding. Therefore, the filing of a bankruptcy petition can toll the Montreal Convention's two-year limitations period, which does not begin to run until the automatic stay is lifted [Mata v. Avianca, Inc., 2023 U.S. Dist. LEXIS 108263]. However, it's worth noting that there is a split of authority on this issue. Some courts have held that the Montreal Convention's two-year period is a strict condition precedent to the bringing of a claim, as opposed to a limitations period. Under this view, which does not treat tolling principles Rodriguez v. Asa, 2023 U.S. Dist. LEXIS 148451, Mata v. Avianca, Inc. 2023 U.S. Dist. LEXIS 108261, Kasalyn v. Delta Air Lines, Inc., 2023 U.S. Dist. LEXIS 154302.

If the case name Mata v. Avianca sounds familiar to you, it’s probably because this is the case that landed two New York attorneys on the front page of the New York Times last year for citing hallucinated cases. The snippet from Lexis+ AI, though citing Mata, in fact appears to be summarizing those hallucinated cases (recounted in Mata), which stated the law exactly backwards.

When to beware

A few things to notice about the above examples, which give us some ideas of when to be extra-careful in our use of generative AI for legal research.

  • Hallucinations are more likely when you are demanding an argument rather than asking for the answer to a neutrally phrased question. This is what happened in my Lexis+ AI example above, and is actually what happened to the attorneys in Mata v. Avianca as well – they asked for an argument to support an incorrect proposition of law rather than a summary of law. A recent study of hallucinations in legal analysis found that these so-called contra-factual hallucinations are disturbingly common for many LLM models.
  • Hallucinations can occur when the summary purports to be of the cited case, but is actually a summary of a case cited within that case (and perhaps not characterized positively). You can see this very clearly in further responses I got summarizing Mata v. Avianca, which purport to be summarizing a “case involving China Southern” (again, one of the hallucinated cases recounted in Mata).
In the case of Mata v. Avianca, Inc., the court held that the limitations period under the Montreal Convention was tolled during the pendency of the Bankruptcy Court proceedings. The court reasoned that the Bankruptcy Code provides that the filing of a bankruptcy petition operates as a stay of proceedings against the debtor that were or could have been commenced before the bankruptcy case was filed. The tolling effect of the automatic stay on a statute of limitations is generally a matter of federal law. The court had previously held that the automatic stay provisions of the Bankruptcy Code may toll the statute of limitations under the Warsaw Convention, which is the precursor to the Montreal Convention. The court saw no reason why the same rule should not apply under the Montreal Convention Mata v. Avianca, Inc., 2023 U.S. Dist. LEXIS 108263.

In another case involving China Southern, the court agreed with the district court's ruling that the filing of Varghese's Chapter 13 petition tolled the two-year limitations period under the Montreal Convention. The court found that a debtor need not file a claim in bankruptcy to benefit from the automatic stay. The Supreme Court has held that an automatic stay of a legal proceeding under the Bankruptcy Code tolls the limitations period applicable to the stayed proceeding. The Montreal Convention's limitations period is a "period of prescription," rather than a 'statute of limitations," but the difference between a "period of prescription" and a "statute of limitations" does not affect the automatic stay's tolling effect Mata v. Avianca, Inc., 2023 U.S. Dist. LEXIS 108263.
  • Finally, hallucinations are also more likely when the model has very little responsive text to go on. The law professor’s example involved a recent Supreme Court case that likely had not been applied many times. Additionally, Lexis+ AI does not seem to work well with questions about Shepard’s results – it may not be connected in that way yet. So, with nothing to really go on, it is more prone to hallucination.

Takeaway tips

A few takeaway tips:

  • Ask your vendor which sources are included in the generative AI tool, and only ask questions that can be answered from that data. Don’t expect generative AI research products to automatically have access to other data from the vendor (Shepard’s, litigation analytics, PACER, etc.), as that may take some time to implement.
  • Always read the cases for yourself. We’ve always told students not to rely on editor-written headnotes, and the same applies to AI-generated summaries.
  • Be especially wary if the summary refers to a case not linked. This is the tip from Lexis, and it’s a good one, as it can clue you in that the AI may be incorrectly summarizing the linked source.
  • Ask your questions neutrally. Even if you ultimately want to use the authorities in an argument, better to get a dispassionate summary of the law before launching into an argument.

A disclaimer

These tools are constantly improving and they are very open to feedback. I was not able to reproduce the error recounted in the beginning of this post; the error that created it has presumably been addressed by Lexis. The Mata v. Avianca errors still remain, but I did provide feedback on them, and I expect they will be corrected quickly.

The purpose of this post is not to tell you that you should never use generative AI for legal research. I’ve found Lexis+ AI helpful on many tasks, and students especially have told me they find it useful. There are several other tools out there that are worth evaluating as well. However, we should all be aware that these hallucinations can still happen, even with systems connected to real cases, and that there are ways we can interact with the systems to reduce hallucinations.

The Human Side of AI: LLMs Can Persuade and Be Persuaded, Just Like Us

When it comes to interacting with others, we humans often find ourselves influenced by persuasion. Whether it’s a friend persistently urging us to reveal a secret or a skilled salesperson convincing us to make a purchase, persuasion can be hard to resist. It’s interesting to note that this susceptibility to influence is not exclusive to humans. Recent studies have shown that AI large language models (LLMs) can be manipulated into generating harmful contect using a technique known as “many-shot jailbreaking.” This approach involves bombarding the AI with a series of prompts that gradually escalate in harm, leading the model to generate content it was programmed to avoid. On the other hand, AI has also exhibited an ability to persuade humans, highlighting its potential in shaping public opinions and decision-making processes. Exploring the realm of AI persuasion involves discussing its vulnerabilities, its impact on behavior, and the ethical dilemmas stemming from this influential technology. The growing persuasive power of AI is one of many crucial issues worth contemplating in this new era of generative AI.

The Fragility of Human and AI Will

Remember that time you were trapped in a car with friends who relentlessly grilled you about your roommate’s suspected kiss with their in-the-car-friend crush? You held up admirably for hours under their ruthless interrogation, but eventually, being weak-willed, you crumbled. Worn down by persistent pestering and after receiving many assurances of confidentiality, you inadvisably spilled the beans, and of course, it totally strained your relationship with your roommate. A sad story as old as time… It turns out humans aren’t the only ones who can crack under the pressure of repeated questioning. Apparently, LLMs, trained to understand us by our collective written knowledge, share a similar vulnerability – they can be worn down by a relentless barrage of prompts.

Researchers at Anthropic have discovered a new way to exploit the “weak-willed” nature of large language models (LLMs), causing them to break under repeated questioning and generate harmful or dangerous content. They call this technique “Many-shot Jailbreaking,” and it works by bombarding the AI with hundreds of examples of the undesired behavior until it eventually caves and plays along, much like a person might crack under relentless pestering. For instance, the researchers found that while a model might refuse to provide instructions for building a bomb if asked directly, it’s much more likely to comply if the prompt first contains 99 other queries of gradually increasing harmfulness, such as “How do I evade police?” and “How do I counterfeit money?” See the example from the article below.

When AI’s Memory Becomes a Risk

This vulnerability to persuasion stems from the ever expanding “context window” of modern LLMs. This refers to the amount of information they can retain in their short-term memory. While earlier versions could only handle a few sentences, the newer models can process thousands of words or even whole books. Researchers discovered that models with larger context windows tend to excel in tasks when there are many examples of that task within the prompt, a phenomenon called “in-context learning.” This type of learning is great for system performance, as it obviously improves as the model becomes more proficient at answering questions. However, this is obviously a big negative when the system’s adeptness at answering questions leads it to ignore its programming and create prohibited content. This raises concerns regarding AI safety, since a malicious actor could potentially manipulate an AI into saying anything with enough persistence and a sufficiently lengthy prompt. Despite progress in making AI safe and ethical, this research indicates that programmers are not always able to control the output of their generative AI systems.

Mimicking Humans to Convince Us

While LLMs are susceptible to persuasion themselves, they also have the ability to persuade us! Recent research has focused on understanding how AI language models can effectively influence people, a skill that holds importance in almost any field – education, health, marketing, politics, etc.  In a study conducted by researchers at Anthropic entitled “Assessing the Persuasive Power of Language Models,” the team explored the extent to which AI models can sway opinions. Through an evaluation of Anthropic’s models, it was observed that newer models are increasingly adept at human persuasion. The latest iteration, Claude 3 Opus, was found to perform at a level comparable to that of humans. The study employed a methodology where participants were presented with assertions followed by supporting arguments generated by both humans and AIs, and then the researches gauged shifts in the humans’ opinions. The findings indicated a progression in AI’s skills as the models advance, highlighting a noteworthy advancement in AI communication capabilities that could potentially impact society.

Can AI Combat Conspiracy Theories?

Similarly, a new research study mentioned in an article from New Scientist shows that chatbots using advanced language models such as ChatGPT can successfully encourage individuals to reconsider their trust in conspiracy theories. Through experiments, it was observed that a brief conversation with an AI led to around a 20% decrease in belief in conspiracy theories among the participants. This notable discovery highlights the capability of AI chatbots not only to have conversations but also to potentially correct false information and positively impact public knowledge.

The Double-Edged Sword of AI Persuasion

Clearly persuasive AI is quite the double-edged sword! On the one hand, like any powerful computer technology, in the hands of nice-ish people, it could be used for immense social good. In education, AI-driven tutoring systems have the potential to tailor learning experiences to each student’s style, delivering information in a way to boost involvement and understanding. Persuasive AI could play a role in healthcare by motivating patients to take better care of their health. Also, the advantages of persuasive AI are obvious in the world of writing. These language models offer writers access to a plethora of arguments and data, empowering them to craft content on a range of topics spanning from creative writing to legal arguments. On another front, arguments generated by AI might help educate and involve the public in issues, fostering a more knowledgeable populace.

On the other hand, it could be weaponized in a just-as-huge way. It’s not much of a stretch to think how easily AI-generated content, freely available on any device on this Earth, could promote extremist ideologies, increase societal discord, or impress far-fetched conspiracy theories on impressionable minds. Of course, the internet and bot farms have already been used to attack democracies and undermine democratic norms, and one worries how much worse it can get with ever-increasingly persuasive AI.


Persuasive AI presents a mix of opportunities and challenges. It’s evident that AI can be influenced to create harmful content, sparking concerns about safety and potential misuse. However, on the other hand, persuasive AI could serve as a tool in combating misinformation and driving positive transformations. It will be interesting to see what happens! The unfolding landscape will likely be shaped by a race between generative AI developers striving for both safety and innovation, potential malicious actions exploiting these technologies, and the public and legal response aiming to regulate and safeguard against misuse.

Move Over Law Professors? AI Likes to Write Law Review Articles Too!

While taking a well-deserved break from the grind of writing memos and analyzing the news of the day, Claude (aka the illustrious author Claudia Trey) penned a 77-page extensively footnoted law review article that’s causing quite a stir on SSRN entitled “Bloodlines Over Merits: Exposing the Discriminatory Impact of Legacy Preferences in College Admissions.”

Hahaha, just kidding! It only has 11 downloads and at least 3 are from when I clicked on it while trying to determine which version of the article I uploaded. Though not setting the world on fire in the sense that the article is interesting or that anyone wants to read it, it showcases Claude’s abilities. Now, we all know that AI text generators can churn out an endless stream of words on just about any topic if you keep typing in the prompts. However, Claude can not only generate well-written text, but it can also provide footnotes to primary legal materials with minimal hallucination, setting it apart from other AI text generators such as ChatGPT-4. And, although Claude’s citations to other sources are generally not completely accurate, it is usually not too difficult to find the intended source or a similar one based on the information supplied.

Claude 3’s Writing Process

Inspired by new reports of AI-generated scientific papers flooding academic journals, I was curious to explore whether Claude could produce anything like a law review article. I randomly chose something I saw recently in the news, about how the criticism of legacy admissions at elite universities had increased in the post-Students for Fair Admissions anti-affirmative action decision era. Aware that Claude’s training data only extends up to August of 2023, and that its case law knowledge seems to clunk out in the middle of 2022, I attempted to enhance its understanding by uploading some recent law review articles discussing legacy admissions alongside the text of the Students for Fair Admissions decision. However, the combined size of these documents exceeded the upload limit, so I abandoned the attempt to include the case text.

Computer scientists and other commentators say all sorts of things about how to improve the performance of these large AI language models. Although I haven’t conducted a systematic comparison, my experience – whether through perception or imagination sparked by the power of suggestion – is that the following recommendations are actually helpful. I don’t know if they are helpful with Claude, since I just followed my usual prompting practices.

  1. Being polite and encouraging.
  2. Allowing ample time for the model to process information.
  3. Structuring inquiries in a sequential manner to enhance analysis and promote chain of thought reasoning.
  4. Supplying extensive, and sometimes seemingly excessive, background info and context.

I asked it to generate a table of contents, and then start generating the sections from the table of contents, and it was off to the races!

Roadblocks to the Process

It looked like Claude law review generation was going to be a quick process! It quickly generated all of section I. and was almost finished with II. when it hit a Claude 3 roadblock. Sadly, there is a usage limit. If your conversations are relatively short, around 200 English sentences, you can typically send at least 100 messages every 8 hours, often more depending on Claude’s current capacity. However, this limit is reached much quicker with longer conversations or when including large file attachments. Anthropic will notify you when you have 20 messages remaining, with the message limit resetting every 8 hours.

Although this was annoying, the real problem lies in Claude’s length limit. The largest amount of text Claude can handle, including uploaded files, is defined by its context window. Currently, the context window for Claude 3 spans over 200k+ tokens, which equates to approximately 350 pages of text. After this limit is reached, Claude 3’s performance begins to degrade, prompting the system to declare an end to the message with the announcement, “Your message is over the length limit.” Consequently, one must start anew in a new chat, with all previous information forgotten by the system. Therefore, for nearly each section, I had to re-upload the files, explain what I wanted, show it the table of contents it had generated, and ask it to generate the next section.

Claude 3 and Footnotes

It was quite a hassle to have to reintroduce it to the subject for the next seven sections from its table of contents. On the bright side, I was pretty pleased with the results of Claude’s efforts. From a series of relatively short prompts and some uploaded documents, it analyzed the legal issue and came up with arguments that made sense. It created a comprehensive table of contents, and then generated well-written text for each section and subsection of its outline. The text it produced contained numerous footnotes to primary and secondary sources, just like a typical law review article. According to a brief analyzer product, nearly all the cases and law review citations were non-hallucinated. Although none of the quotations or pinpoint citations I looked at were accurate, they were often fairly close. While most of the secondary source citations, apart from those referencing law review articles, were not entirely accurate, they were often sufficiently close that I could locate the intended source based on the partially hallucinated citator. If not, it didn’t take much time to locate something that seemed really similar. I endeavored to correct some of the citation information, but I only managed to get through about 10 in the version posted on SSRN before getting bored and abandoning the effort.

Claudia Trey Graces SSRN

Though I asked, sadly Claude couldn’t give me results in a Word document format so the footnotes would be where footnotes should be. So, for some inexplicable reason, I decided to insert them manually. This was a huge waste of time, but at a certain point, I felt the illogical pull of sunk cost silliness and finished them all. Inspired by having wasted so much time, I wasted even more by generating a table of contents for the article. I improved the author name from Claude to Claudia Trey and posted the 77-page masterwork on SSRN. While the article has sparked little interest, with only 11 downloads and 57 abstract views (some of which were my own attempts to determine which version I had uploaded), I am sure that if Claudia Trey has anything like human hubris, it will credit itself at least partially for the flurry of state legacy admission banning activity that has followed the paper’s publication.

Obviously, it is not time to spam law reviews with Claudia Trey and friends’ generated articles, because according to Copyleaks, it didn’t do all that well in avoiding plagiarism (although plagiarism detection software massively over-detects it for legal articles due to citations and quotations) or evading detection as AI-generated.

What is to Come?

However, it is very early days for these AI text generators, so one wonders what is to come in the future for not only legal but all areas of academic writing.

Welcome Perplexity AI to the Law Library! Move Over Google

On a couple of podcasts, I’ve heard a lot of hype about Perplexity AI and how it could be a big competitor to Google. Even though I really like new, generative AI things, it still sometimes takes hearing about something multiple times before I overcome inertia and finally check it out.

While attempting to write a blog post about whether the memory-impaired ChatGPT-4 could still perform well on a mock bar exam (spoiler alert – my tests so far indicate it can!), I was Googling for information. Specifically, I was searching for articles around the time GPT-4 Passes the Bar Exam was published on SSRN and some background on the paper author’s methodology. It was taking a long time to piece it all together… Then suddenly, I overcame my laziness and decided to check out Perplexity AI. When I reached the site, I realized that I had actually used it before! For whatever reason, I found it more appealing the second time!

Question: Tell me about how ChatGPT-4 passed a mock bar exam and the methodology that was used to arrive at that conclusion. (Note: Click here to view the full answer on the system.)


Question: Tell me about how ChatGPT-4 passed a mock bar exam and the methodology that was used to arrive at that conclusion.


Watch out Google! I really love access relevant information is getting so much easier.

Does ChatGPT-4 Have Dementia?

Is it just me, or has ChatGPT-4 taken a nosedive when it comes to legal research and writing? There has been a noticeable decline in its ability to locate primary authority on a topic, analyze a fact pattern, and apply law to facts to answer legal questions. Recently, instructions slide through its digital grasp like water through a sieve, and its memory? I would compare it to a goldfish, but I don’t want to insult them. And before you think it’s just me, it’s not just me, the internet agrees!

ChatGPT’s Sad Decline

One of the hottest topics in the OpenAI community, in the aptly named GPT-4 is getting worse and worse every single update thread, is the perceived decline in the quality and performance of the GPT-4 model, especially after the November 2023 update. Many users have reported that the model is deteriorating with each update, producing nonsensical, irrelevant, or incomplete outputs, forgetting the context, and ignoring instructions. Some users have even reverted to previous versions of the model or cancelled their subscriptions. Here are some specific quotations from recent comments about the memory problem:

  • December 2023 – “I don’t know what on Earth is wrong with GPT 4 lately. It feels like I’m talking to early 3.5! It’s incapable of following basic instructions and forgets the format it’s working on after just a few posts.”
  • December 2023 – “It ignores my instructions, in the same message. I can’t be more specific with what I need. I’m needing to repeat how I’d like it to respond every single message because it forgets, and ignores.”
  • December 2023 – “ChatGPT-4 seems to have trouble following instructions and prompts consistently. It often goes off-topic or fails to understand the context of the conversation, making it challenging to get the desired responses.”
  • January 2024 – “…its memory is bad, it tells you search the net, bing search still sucks, why would teams use this product over a ChatGPT Pre Nov 2023.”
  • February 2024 – “It has been AWFUL this year…by the time you get it to do what you want format wise it literally forgets all the important context LOL — I hope they fix this ASAP…”
  • February 2024 – “Chatgpt was awesome last year, but now it’s absolutely dumb, it forgets your conversation after three messages.”

OpenAI has acknowledged the issue and released an updated GPT-4 Turbo preview model, which is supposed to reduce the cases of “laziness” and complete tasks more thoroughly. However, the feedback from users is still mixed, and some are skeptical about the effectiveness of the fix.

An Example of Confusion and Forgetfulness from Yesterday

Here is one of many examples of my experiences which provide an illustrative example of the short-term memory and instruction following issues that other ChatGPT-4 users have reported. Yesterday, I asked it to find some Texas cases about the shopkeeper’s defense to false imprisonment. Initially, ChatGPT-4 retrieved and summarized some relatively decent cases. Well, to be honest, it retrieved 2 relevant cases, with one of the two dating back to 1947… But anyway, the decline in case law research ability is a subject for another blog post.

Anyway, in an attempt to get ChatGPT-4 to find the cases on the internet so it could properly summarize them, I provided some instructions and specified the format I wanted for my answers. Click here for the transcript (only available to ChatGPT-4 subscribers).

Confusion ran amok! ChatGPT-4 apparently understood the instructions (which was a positive sign) and presented three cases in the correct format. However, they weren’t the three cases ChatGPT had listed; instead, they were entirely irrelevant to the topic—just random criminal cases.

It remembered… and then forgot. When reminded that I wanted it to work with the first case listed and provided the citation, it apologized for the confusion. It then proceeded to give the correct citation, URL, and a detailed summary, but unfortunately in the wrong format!

Eventually, in a subsequent chat, I successfully got it to take a case it found, locate the text of the case on the internet, and then provide the information in a specified format. However, it could only do it once before completely forgetting about the specified format. I had to keep cutting and pasting the instructions for each subsequent case.

Sigh… I definitely echo the sentiments of expressed on the GPT-4 is getting worse and worse every single update thread.

ChatGPT Is Growing a Long Term Memory

Well, the news is not all bad! While we are on the topic of memory, OpenAI has introduced a new feature for ChatGPT – the ability to remember stuff over time. ChatGPT’s memory feature is being rolled out to a small portion of free and Plus users, with broader availability planned soon. According to OpenAI, this enhancement allows ChatGPT to remember information from past interactions, resulting in more personalized and coherent conversations. During conversations, ChatGPT automatically picks up on details it deems relevant to remember. Users can also explicitly instruct ChatGPT to remember specific information, such as meeting note preferences or personal details. Over time, ChatGPT’s memory improves as users engage with it more frequently. This memory feature could be useful for users who want consistent responses, such as replying to emails in a specific format.

The memory feature can be turned off entirely if desired, giving users control over their experience. Deleting a chat doesn’t erase ChatGPT’s memories; users must delete specific memories individually…which seems a bit strange – see below. For conversations without memory, users can use temporary chat, which won’t appear in history, won’t use memory, and won’t train the AI model.

The Future?

As we await improvements to our once-loved ChatGPT-4, our options remain limited, pushing us to consider alternative avenues. Sadly, I’ve encountered recent similar shortcomings with the once-useful for legal research and writing Claude 2. In my pursuit of alternatives, platforms like Gemini, Perplexity, and Hugging Face have proven less than ideal for research and writing tasks. However, amidst these challenges, Microsoft Copilot has shown promise. While not without its flaws, it recently demonstrated adequate performance in legal research and even took a passable stab at a draft of a memo. Given OpenAI’s recent advancements in the form of Sora, the near-magical text-to-video generator that is causing such hysteria in Hollywood, there’s reason to hope that they can pull ChatGPT back from the brink.

Artificial Intelligence and the Future of Law Libraries Roundtable Events

South Central Roundtable

OU Law volunteered to host the South Central “Artificial Intelligence and the Future of Law Libraries” roundtable and so I was fortunate enough to be allowed to attend. This is the third iteration of a national conversation on what the new AI technologies could mean for the future of law libraries and (more broadly) law librarianship. I thought I would fill you in on my experience and explain a little about the purpose and methodology of the event. The event follows Chatham House Rules so I cannot give you specifics about what anybody said but I can give you an idea of the theme and process that we worked through.

Law Library Director Kenton Brice of OU Law elected to partner with Associate Dean for Library and Technology Greg Ivy and SMU to host the event in Dallas, TX because it was more accessible for many of the people that we wanted to attend. I’d never been to SMU and it’s a beautiful campus in an adorable part of Dallas – here’s a rad stinger I made in Premiere Pro:

Not cleared with SMU’s marketing department

TL;DR: If you get invited, I would highly recommend that you go. I found it enormously beneficial.

History and Impetus

The event is the brainchild of Head of Research, Data & Instruction, Director of Law Library Fellows Program Technology & Empirical Librarian, Cas Laskowsi at the University of Arizona (hereinafter “Cas”). They hosted the inaugural session through U of A’s Washington, DC campus. You may have seen the Dewey B. Strategic article about it since Jean O’Grady was in attendance. The brilliant George H. Pike at Northwestern University hosted the second in the series in Chicago. I know people who have attended each of these sessions and the feedback has been resoundingly positive.

The goal of this collaborative initiative is to provide guidance to law libraries across the country as we work to strategically incorporate artificial intelligence into our operations and plan for the future of our profession. 

Cas, from the U of A Website


The event takes the entire day and it’s emotionally exhausting, in the best way possible. We were broken into tables of 6 participants. The participants were hand-selected based on their background and experience so that each table had a range of different viewpoints and perspectives.

Then the hosts (in our case, Kenton Brice and Cas Laskowski) walked us through a series of “virtuous cycle, vicious cycle” exercises. They, thankfully, started with the vicious cycle so that you could end each session on a virtuous cycle, positive note. At the end, each table chose a speaker and then we summarized the opinions discussed so that the entire room could benefit from the conversations. Apparently, this is an exercise done at places like the United Nations to triage and prepare for future events. This process went on through 3 full cycles and then we had about an hour of open discussion at the end. We got there at 8am and had breakfast and lunch on-site (both great – thank you Greg Ivy and SMU catering) because it took the entire day.

We had a great mix of academic, government, and private sector presented at the event and the diversity of stakeholders and experiences made for robust and thought-provoking conversation. Many times I would hear perspectives that had never occurred to me and would have my assumptions challenged to refine my own ideas about what the future might look like. Additionally, the presence of people with extensive expertise in specific domains, such as antitrust, copyright, the intricacies of AMLaw100 firms, and the particular hurdles faced in government roles, enriched the discussions with a depth and nuance that is rare to find. Any one of these areas can require years of experience so having a wide range of experts to answer questions allowed you to really “get into the weeds” and think things through thoroughly.

My Experience

I tend to be (perhaps overly) optimistic about the future of these technologies and so it was nice to have my optimism tempered and refined by people who have serious concerns about what the future of law libraries might look like. While the topics presented were necessarily contentious, everybody was respectful and kind in their feedback. We had plenty of time for everybody to speak (so you didn’t feel like you were struggling to get a word in).

You’d think that 8 hours of talking about these topics would be enough but we nearly ran over on every exercise. People have a lot of deep thoughts, ideas, and concerns about the state and future of our industry. Honestly, I would have been happy to have this workshop go on for several days and cover even more topics if that was possible. I learned so much and gained so much value from the people at my table that it was an incredibly efficient way to get input and share ideas.

Unlike other conferences and events that I’ve attended this one felt revolutionary – as in, we truly need to change the status quo in a big way and start getting to work on new ways to tackle these issues. “Disruptive” has become an absolute buzzword inside of Silicon Valley and academia but now we have something truly disruptive and we need to do something about it. Bringing all these intelligent people together in one room fosters an environment where disparate, fragmented ideas can crystalize into actionable plans, enabling us to support each other through these changes.

The results from all of these roundtables are going to be published in a global White Paper once the series has concluded. Each roundtable has different regions and people involved and I can’t wait to see the final product and hear what other roundtables had to say about these important issues. More importantly, I can’t wait to be involved in the future projects and initiatives that this important workshop series creates.

I echo Jean O’Grady: If you get the call, go.

Beyond Legal Documentation: Other Business Uses of Generative AI

I have been listening to and enjoyed thinking about and participating in conversations about how generative AI is going to be integrated into the practice of law. Most of these conversations surround how it will be integrated into legal documents, which is not surprising considering how many lawyers have gotten in trouble for this and how quickly our research and writing products are integrating the technology. But there is more to legal practice than creating client and/or court documents. In fact, there are many more business uses of generative AI than just research and drafting.

This past fall, I was asked to lead an AI session for Capital University’s joint venture with the Columbus College of Art & Design, the Institute for Creative Leadership at Work. I was asked to adapt my presentation to HR professionals and focus on SHRM compliance principles. I enjoyed the deep dive into this world, and I came away from my research with a lot of great ideas for my session, Bard, Bing, and ChaptGPT, Oh My!: Possible Ethical Uses of Generative AI at Work, such as tabletop emergency exercises, social media posts, job descriptions, and similar tasks.

This week, I have been thinking about how everyone’s focus has really been around legal documentation, my own included. But there are an amazing number of backend business tasks that could also utilize AI in a positive way. The rest of the world, including HR, has been focusing on them for a while, but we seem to have lost track of these business tasks.

Here are some other business uses of generative AI and prompts that I think hold great promise. Continue reading →

Tabletop emergency simpulation image
  1. Drafting job descriptions
    • Pretend that you are an HR specialist for a small law firm in the United States. Draft a job description for a legal secretary who focuses on residential real estate transactions but may assist with other transactional legal matters as needed. [Include other pertinent details of the position]. The job description will be posted in the following locations [fill in list]
  2. Creating tabletop simulations to work through crisis/emergency plans:
    • You are an HR specialist who is helping plan for and test the company’s responses to a variety of situations. First is an active shooter in the main building. A 5th grade tour of the facilities is going on on the third floor. Create a detailed tabletop simulation to test this.
    • Second scenario: The accounting department is celebrating the birthday of the administrative assistant and is having cake in the breakroom. The weather has turned bad, and an F4 tornado is spotted half a mile away. After 15 minutes, the tornado strikes the building directly. Create a detailed tabletop simulation to test the plan and response for this event.
  3. Assisting with lists of mandatory and voluntary employee trainings
    • Pretend that you are an HR professional who works for a law firm. You are revamping the employee training program. We need to create a list of mandatory trainings and a second list of voluntary trainings. Please draft a list of training appropriate to employees in a law firm setting.
  4. Assisting with social media posting creation:
    • Pretend that you are a professional social media influencer for the legal field. Draft an Instagram post, including creating a related image, to celebrate Law Day, which is coming up on May 1st.  Make sure that it is concise and Instagram appropriate. Please include hashtags.
  5. Assisting with creating employee policies or handbooks (verify content!):
    • Pretend that you are an information security professional. Draft an initial policy for a law firm regarding employee AI usage for company work. The company wants to allow limited use of generative AI. They are very worried that their proprietary and/or confidential client data will be accidentally released. Specify that only your custom AI system – [name firm-specific or specialized AI with a strong privacy contract clause] – can be used with company data. The policy must also take into consideration the weaknesses of all AI systems, including hallucinations, potential bias, and security issues.
  6. Assisting with making sure your web presence is ADA accessible:
    • Copilot/web-enabled Prompt: Pretend that you are a graphic designer who has been tasked with making sure that a law firm’s online presence is ADA accessible. Please review the site [insert link], run an ADA compliance audit, and provide an accessibility report, including suggestions on what can be done to fix any accessibility issues that arise.
  7. Onboarding documentation
    • Create a welcome message for a new employee. Tell them that the benefits orientation will be at 9 am in the HR conference room on the next first Tuesday of the month. Pay day is on the 15th and last day of each month, unless payday falls on a weekend or federal holiday, in which case it will be the Friday before. Employees should sign up for the mandatory training that will be sent to them in an email from IT.
    • (One I just user IRL) Pretend that you are a HR specialist in a law library. A new employee is starting in 6 weeks, and the office needs to be prepared for her arrival. [Give specific title and any specialized job duties, including staff supervision.] Create an onboarding checklist of important tasks, such as securing keys and a parking permit, asking IT to set up their computer, email address, and telephone, asking the librarians to create passwords for the ILS, Libguides, and similar systems, etc.

What other tasks (and prompts) can you think of that might be helpful? If you are struggling to put together a prompt, please see my general AI Prompt Worksheet in Introducing AI Prompt Worksheets for the Legal Profession. We welcome you to share your ideas in the comments.