"Stewards of Dignity"
In the mid-1990s, Greg Siskind, then a solo immigration lawyer in Memphis, was updating his practice’s website five times a day. That in a state where lawyers were required to submit all advertisements to the bar for pre-approval. The rule was built for yellow pages and print newspaper classifieds. Nobody had figured out how the regulation applied to this new thing — a website — or whether it applied at all. Rather than wait for an answer, he negotiated a workaround: a change-log the state bar could review after the fact—and that allowed him to keep his website going. [Watch LITCon 2026 on Youtube. You can watch in sections.]
Three decades later, Siskind told that story to a room full of legal innovators at Suffolk Law’s LITCon 2026, the annual conference where the law school’s LIT Lab and LIT Center bring together access-to-justice advocates, technologists, and court partners to confront the gap between the legal help Americans need and what they actually get.
Each wave of new technology has brought its own legal ethical worries, Siskind said. Websites would amount to illegal advertising; email would breach confidentiality; social media would create inadvertent attorney-client relationships; and now AI raises countless new objections.
Some of the ethical concerns are real, but they can also paralyze, leaving a lawyer “stuck not innovating because you’re just afraid that somebody’s going to shut it all down.”
In spite of the fears, Siskind has been working on closing the justice gap for three decades. In the early 1990s, he was answering immigration questions on internet forums where no lawyers were present — just immigrants trying to understand a system with almost no publicly available information. His website and email newsletter, launched in 1994, became some of the first places where people could find detailed, plain-language immigration guidance without hiring an attorney.
Today his work has shifted to the lawyer side: Visalaw AI, an immigration-specific research and drafting platform he designed to help attorneys handle cases faster and serve more clients. It’s free for law school clinics and nonprofits.
Cat Moon, co-director of Vanderbilt’s AI Law Lab, put the paralysis argument more bluntly during a panel on innovation labs.
The legal profession struck a bargain, she said: a monopoly on legal practice in exchange for serving as gatekeepers of justice. But the math has never worked, she contends: 1.3 million lawyers, 260 million legal problems; 30 to 40 percent of licensed attorneys don’t even serve individual clients. The profession’s aspirational obligation to help people who can’t pay is exactly that — aspirational, she argued. And suing services like LegalZoom for filling a gap that lawyers won’t fill themselves isn’t a solution. “How are people who we’ve never existed for going to notice we’re gone?”
Sonja Ebron, CEO of Courtroom5, argued that the justice system today is where the electric grid was before rural electrification: designed to serve some communities while leaving minority, rural, and poor areas in the dark. Her platform trains pro se litigants to build their own civil cases. She makes her case for treating baseline litigation competence as public infrastructure in her newsletter, Without Counsel.
The Tools
Those themes ran through a day of more than a dozen presentations over eight hours. A small sampling of what people are building:
- Lois Lupica at the University of Maine demonstrated My Reply, an AI-powered eviction defense tool that reads a tenant’s court papers, identifies up to 140 defenses, and generates a ready-to-file answer.
- Daniel Bernal at Stanford showed that in Los Angeles, 26 percent of default judgments in debt collection cases contained errors that should have blocked the judgment entirely — and unveiled an AI tool that catches what courts miss.
- Scheree Gilchrist at Legal Aid of North Carolina described an AI-powered intake system for a program that fields a huge number of calls each year.
- Jessica Frank at Free Law Project described a litigant portal designed to live on court websites so that a pro se filer at 3 a.m. gets jurisdiction-specific guidance, not whatever a general-purpose chatbot invents.
- Caitlin Reddy at the Massachusetts Trial Court laid out plans for the state’s first online dispute resolution pilot, set to launch in three small claims courts.
- Casey Chiappetta at the Pew Charitable Trusts described a project using large language models to extract structured data from court filings so judges can verify that debt documentation meets legal requirements before entering default judgments — part of Pew’s work with courts in 13 states on debt collection reform.
- Jennifer Barnett at the American Arbitration Association laid out a pilot with a Pennsylvania court to automate debt case diversion — scaling a process currently run by one and a half staffers using Excel and Word.
Turning a Confusing Form into a Lifeline
Imagine a MassHealth member named Maria. She’s been on insulin for years, and one day learns her prescription coverage has been denied. Her doctor confirms the medication is still medically necessary. She has 60 days to appeal. Without coverage, she can’t afford the insulin. She searches for the document required to start her appeal, the Massachusetts Fair Hearing Request Form, and finds it baffling.
This is the problem Suffolk Law LIT Lab student Elizabeth Clagett set out to solve. The LIT Lab’s Court Forms Online project helps more than 30,000 people a year complete and file legal forms through guided online interviews, TurboTax style, built on the free, open-source platform Docassemble.
Clagett used the tool to make the MassHealth form user-friendly. Instead of presenting everything at once, her tool asks a few simple questions first and uses the answers to guide the user to what’s relevant.
Her project was one of a dozen student efforts presented at LITCon 2026. Students from the LIT Lab and Suffolk’s ODR Innovation Clinic, directed by retired Probate and Family Court Chief Justice John D. Casey, are working on two fronts to address the challenges of filing an uncontested divorce.
In partnership with the American Arbitration Association, clinic students customized an AI-powered ODR platform to walk couples through custody, support, and asset division, with answers flowing into a court-approved separation agreement.
At the same time, LIT Lab students built Docassemble guided interviews for the court paperwork itself — financial statements, joint petitions, and complaints. Both tracks are informed by a twice-weekly student clinic at Suffolk County Probate Court.
A LIT Lab fellow working with Suffolk’s Human Rights and Indigenous People’s Clinic helped the Mashpee Wampanoag tribal court draft a harassment protection law while simultaneously building the guided interview tool that would make filing navigable.
Other teams worked on adult guardianship reporting, military affidavits, small claims, and appeals court docketing statements.
LIT Impact Awards
LITCon 2026 marked the tenth anniversary of Docassemble, the free, open-source platform that powers nearly every project the LIT Lab students presented. Its creator, Jonathan Pyle, an attorney at Philadelphia Legal Assistance who built and still maintains Docassemble, was recognized with a tribute. The platform anchors legal aid programs in Illinois, Michigan, Minnesota, and Massachusetts.
The LIT Impact Award, went to Katherine Alteneder Mills. In 2001 she founded the nation’s first virtual self-help center for the Alaska Court System—built to reach people across a state where getting to a courthouse can sometimes mean crossing the tundra. From 2013 to 2022, she led the Self-Represented Litigation Network, now the Access to Justice Network at Stanford Law School, growing it into a nationwide community of more than 2,000 members. In her remarks, Alteneder Mills offered the audience a phrase to carry in their work: “Steward of dignity.” Beneath all the systems and the scale, she said, is a simpler question: “Are we being stewards of dignity in ways big and small?”