A Tool in Your Hands

AI will not save anyone. But in the right hands, used for the right reasons, it can help a person save themselves. Here is what that looks like behind the wall.

By Gregory Ringler

There is more being written about artificial intelligence right now than almost anything, and close to none of it comes from people who spend much time thinking about life behind the wall. So let me be straight with you. Strip away the hype and the fear, and what is left is a tool. A tool is only worth what the hands holding it make of it, and the question worth your time is a practical one: what can you get it to do for you? For someone who is incarcerated or coming home, the answer turns out to be a lot.

Start with learning, because that is where the leverage is. The most useful thing AI does is explain, at whatever level you need it, as many times as you need it, without ever making you feel small for asking. Have it break down a word, a paragraph, or an entire book. Run the math you missed in school past it. Let it show you how a business plan is put together, or quiz you for the GED until the material finally sticks. The Last Mile has already proven that people inside can learn to code and build real careers with no internet access at all. AI takes that a step further by turning studying into a conversation, and for anyone teaching themselves, that is the difference between hitting a wall and getting unstuck.

Then there is the paperwork the system seems designed to make unreadable. Anyone who has tried to get through a legal filing, a DOC policy, or a page of parole conditions knows that language was never written for regular people to follow. AI is good at taking a dense, intimidating document and laying it back out in plain English. Courts in several states are already testing AI assistants that help people without lawyers understand their cases and complete the right forms, some of them built on the same tools available to anyone today. It is no substitute for a real attorney, and you should never lean on it as your only source, because AI can be confidently wrong and every fact, date, and citation has to be checked against the record. But for understanding what you are actually holding before you walk into a courtroom or a hearing, it helps level a field that has always tilted the other way.

Here is where it gets interesting for the people who read this newsletter. The incarcerated leaders profiled in these pages are building nonprofits, grassroots programs, and income from the inside, and every bit of that runs on writing: grant proposals, mission statements, budgets, bylaws, outreach letters, program outlines. AI can draft any of it. Describe your idea in your own words and it hands you back a first version to cut and reshape, which can turn a month of staring at a blank page into an afternoon of real progress. The vision still has to come from you. What the tool does is carry the weight of getting that vision onto the page in language funders and partners will take seriously.

The same goes for coming home. AI can build a résumé out of a rough work history, write a cover letter, run mock interviews until the nerves settle, and make sense of a confusing job posting or benefits form. In a market where almost everything now moves through a screen, just being comfortable with these tools is a skill worth real money.

Now the part the hype skips. Most facilities still block the open internet, tablets can be limited or expensive, and anything you type on a monitored device should be treated as something the facility can read. AI gets things wrong too, sometimes badly, so treat it as a place to start and never the final word. None of that cancels the opportunity. If anything, it makes the case sharper. Knowing what these tools can and cannot do, and pressing the institutions around you for fair and safe access to them, is part of the same fight this newsletter has always carried: stop waiting for the outside world to hand you power, and start building it yourself.

These tools are here now, and they only get more capable from here. The people who learn to work with them early will walk into courtrooms, interviews, and funding meetings better prepared than the system ever meant for them to be. So pick the tool up, and put it to work.

Gregory Ringler is a technology founder who builds AI tools and a full-stack developer volunteer with the United Black Family Scholarship Foundation (UBFSF). He writes on technology and its uses for people and communities too often left out of it.




Gregory Ringler Full-Stack Developer & Volunteer · United Black Family Scholarship Foundation (UBFSF) ubfsf.org · zomediaproductions.com · Gregory@ubfsf.org Advocating for education, justice, and community empowerment. UBFSF is a registered 501(c)(3) nonprofit organization.

Sources

• The Last Mile — Digital Literacy in Prisons: Preparing for Reentry in the Age of Technology: https://thelastmile.org/digital-literacy-in-prisons-reentry-technology/
• The Last Mile (program overview): https://thelastmile.org/
• Thomson Reuters Institute — Chatbots for justice: The impact of AI-driven tools for pro se litigants: https://www.thomsonreuters.com/en-us/posts/ai-in-courts/chatbots-pro-se-litigants/
• Thomson Reuters Institute — When courts meet GenAI: Guiding self-represented litigants through the AI maze: https://www.thomsonreuters.com/en-us/posts/ai-in-courts/guiding-self-represented-litigants/
• American Bar Association — Access to Justice 2.0: How AI-powered software can bridge the gap: https://www.americanbar.org/groups/journal/articles/2025/access-to-justice-how-ai-powered-software-can-bridge-the-gap/