Sending Letters to Incarcerated People Is Too Hard. This App Makes It Easy

The latest addition to robo-lawyer app DoNotPay is a service for sending physical mail to people in prisons.
Letters image via Getty Images ​
Image via Getty Images

For five years, law student-turned tech entrepreneur Joshua Browder has been creating robo-lawyers and chatbots that help with some of life's most annoying little problems: canceling free trials, cancelling and suing robocallers, fighting parking tickets.

Now, he's turned the DoNotPay platform—an app launched in 2016 that encompasses all of the above AI-powered services—on the prison mail-sending complex. The new prison mailing product, which goes live today, aims to solve the problem of complicated and expensive mail systems for incarcerated people and their families.


Letter-sending to prisons is often a maze of requirements and bureaucracy that gets something as simple as a greeting card rejected—some prisons won't allow mail that contains perfume, marker or crayon drawings, or paint, while others ban greeting cards and postcards with any graphic designs. By automating the process of formatting and sizing letters according to facility's rules, DoNotPay is working to lower the chance that mail will be rejected for these sorts of rules, and that the message eventually gets to their loved ones inside.

"I've been working on DoNotPay, trying to replace exploitative industries, and I only work on things that affect billions of people," Browder told Motherboard. "What I discovered is that more people are under the control of the prison system than get parking tickets." More than 2.3 million people are held in the criminal justice system in 2020, according to the Prison Policy Initiative.

Screenshot of the DoNotPay app

Screenshot of the DoNotPay app

It's a big enough problem that other app-makers are taking on the issue. Ameelio, a nonprofit with funding from organizations including Mozilla and Schmidt Futures, similarly uses an online database to locate incarcerated people and then walks users through steps to write and send letters. These apps are taking on for-profit companies like JPay, which charges inflated prices for postage and make it harder to communicate with loved ones outside—while making millions in profits and state partnerships.

On DoNotPay, users can find their loved ones at any federal, state, county, or ICE detention center, Browder said, by using a search tool that looks them up through the otherwise varied and complicated government-run databases. From there, they can choose from a variety of designs and send a custom letter that will be printed and mailed according to their specific facility's requirements for incoming mail. The letters come with return-addressed postage so that the recipient can send a letter back.

What's in the letter, however, is up to the message-sender. Browder said that DoNotPay doesn't read or scan contents of letters, for the privacy of both parties.

The DoNotPay app costs $3 a month, with no extra charge for the prison mailing features.