The Technology Shock of Re-entry After Prison

By Sam Bufe, Sr. Manager of Research and Analytics at The Last Mile.

AI is transforming everyday work, leaving many modern workers startled—or even frightened—by the pace of change.

Imagine waking up one morning to find that everyone in your life has jumped ten years into the technological future. The phones are different. The apps are different. The way people apply for jobs, pay for groceries, and contact their kids’ teachers has moved on without you. You’re expected to keep up as though no time has passed.

For many people coming home from prison, that isn’t a thought experiment. It’s the first week out.

Among all the barriers that returning citizens face—housing, employment, finances–few are as disorienting and intimidating as the technology shock: re-entering a world that has completely rebuilt itself around technology you never got to learn. The tasks that are supposed to be the first steps toward stability — applying for a job, enrolling in a class, setting up direct deposit, booking an appointment — now assume a level of digital fluency and access that most returned citizens simply haven’t had the chance to build.

Returning Citizens Need Technology Skills AND Access

Closing the digital divide after prison takes two things, and neither one works without the other.

The first is physical access to technology: the computers and connectivity you actually need to continue your education and pursue high-quality employment. To compete in today’s economy, returning citizens need regular access to the same industry-standard technology they’ll be expected to use on the job, which means laptops and productivity-enhancing software and not just smartphones with an internet connection.

The second is the skills to use that technology. You can hand someone a laptop, but if they’ve spent years without one, they still face an enormous learning curve – one that many of us can barely imagine because we have spent our lives growing alongside this technology. Real digital fluency — the kind that lets you navigate an application portal or troubleshoot your way through an online class — is built not through a short weekend course but by spending significant time working through problems using that technology.

Give someone access without skills, and the hardware collects dust. Give someone skills without access, and the training has nowhere to go. 

Closing the Digital Divide Before Release

This is why so much of our work at The Last Mile starts inside. In our classrooms, we work with people while they are still incarcerated to make sure they gain real, hands-on experience with technology so that the “technology shock” at release isn’t nearly so stark.

Unlike so many in-prison programs, TLM is an immersive technology-oriented experience where students spend 25+ hours a week working through real-world tasks using modern technology that employers are using every day outside the walls of a prison. By contrast, the average associates degree program in California typically requires 3 hours a week in a classroom over the course of 9 years.

In TLM classrooms right now, students are learning modern coding languages, audio-visual editing programs, video game development, as well as entrepreneurship, project management, marketing, and beyond. They are working through assignments that are designed to be difficult and frustrating but with the ultimate goal of ensuring that TLM alumni walk out of prison confident that they have mastered the tools that successful reentry demands.

That preparation can reduce the learning curve, but digital fluency can only carry someone so far if they return home without the technology needed to put it to use. To understand how often that happens, our reentry team looks at the devices and internet connectivity alumni have when they first come home.

The data reveals a divide that is less about getting online and more about having the right tools to pursue meaningful education and employment.

What Our Returning Citizen Survey Data Shows

When people first get in touch with us after release, our baseline survey shows exactly where the divide sits — and it isn’t where you might expect.

The vast majority already have some form of internet connectivity. When they first make contact with our reentry team, about 86% of TLM alumni have a smartphone and roughly 91% have some form of internet access — nearly on par with the general population. 

However, there is a very real gap in terms of access to computers – the technology that is needed to meaningfully leverage the opportunities offered by internet connectivity. Only about 23% of our returning citizens have a desktop or laptop at home, compared to roughly 78% of U.S. households.

In other words, people are overwhelmingly smartphone-dependent: they can browse and text, but only about one in four has the kind of device you actually need to search and apply for jobs, write a resume, or take an online course.

Closing the gap on both fronts

The Last Mile is addressing the other half of the equation too: we get laptops into the hands of our alumni when they come home. Paired with the digital skills they build before release, it means people arrive on the outside with both the ability and the tools to use it.

We think that’s a winning formula — skills plus physical technology — to shrink the technology shock of reentry, and to give returning citizens a real shot at the education and employment that a modern economy runs on.

Every returning citizen deserves the opportunity to come home prepared—not only to navigate a technology-driven world, but to build a stable and fulfilling future within it. Closing the digital divide requires educators, employers, technology leaders, funders, and community partners working together to expand access and opportunity.

If you are interested in contributing to this mission or exploring a partnership with The Last Mile, contact us and help ensure that the prison gate never becomes a barrier to the modern world.

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By Sam Bufe, Sr. Manager of Research and Analytics at The Last Mile.

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