Hidden Barriers: Technology & Reentry

A man walks into a job center. He’s motivated and ready to work. The staff member hands him a tablet and says, “Just fill out the application online.” He stares at the screen. He hasn’t touched a smartphone since 2011. There was no swipe, no app icons, no autocorrect back then. Flip phones still ruled. Now he’s supposed to create an email account, upload a resume as a PDF, and pass a CAPTCHA test, all before lunch.

This scene plays out every day at reentry programs across the country. And it rarely gets the attention it deserves.

Time Doesn’t Pause

When someone is incarcerated for five, ten, or twenty years, the world outside doesn’t wait for them. It sprints ahead. Cash gives way to Venmo. Paper job applications give way to online portals with dropdown menus and required fields. Physical bank branches shrink while apps take over. Even ordering food or catching a ride now runs through a phone.

For someone stepping back into that world, the gap isn’t just inconvenient. It’s disorienting. Imagine missing every operating system update, every app redesign, every shift in how people communicate, all at once. That’s the reality for many people with legal histories, and it touches nearly everything they need to rebuild a life: housing applications, medical appointments, unemployment benefits, even talking to their own kids.

Researchers have a name for this. Bianca Reisdorf and Julia DeCook, who study digital inclusion, call it a form of “compound vulnerability.” Their 2022 study in New Media & Society found that people leaving incarceration face overlapping disadvantages, limited digital skills stacked on top of low income, spotty education access, and, for many, age or disability. None of these problems live in isolation. They compound.

And this isn’t a niche issue. In North Carolina alone, roughly 95 percent of people in state prisons will eventually come home, about 18,000 people a year, according to state reentry data cited by North Carolina Health News. Multiply that across the country and the scale becomes clear. This is a mainstream reentry challenge, not an edge case.

Where the Barriers Actually Show Up

It helps to get specific, because “digital divide” as a phrase doesn’t capture what’s actually happening day to day.

Job searching has moved almost entirely online. By 2025, roughly 80 percent of job searches happened online, according to labor market research firm Zippia. Applications that used to take a walk-in and a handshake now require an account on a job board, a formatted resume, and often a personality assessment buried three clicks deep. Researchers at the University of Michigan studied this exact problem and found that digital literacy gaps directly undermine job searches for returning citizens, motivating them to build targeted digital literacy tools specifically for this population. Someone who has never used a mouse is suddenly expected to navigate it all solo.

Banking has changed shape. Direct deposit, mobile check scanning, and two-factor authentication through text message. These aren’t optional extras anymore; they’re often required to even open an account or access wages.

Identification itself has gone digital. Some states now push digital IDs. Government benefits portals require login credentials, security questions, and email verification. A person without a stable address or a working phone number can get stuck at step one. A recent study on formerly incarcerated older adults applying for Social Security disability benefits found applications routinely stalled for six months to a year, with digital unfamiliarity named as one of the recurring hurdles, on top of missing paperwork and inconsistent guidance from caseworkers.

Scams and misinformation are everywhere. People who’ve been away don’t have years of accumulated street smarts about phishing emails or fake job offers. That makes them easy targets right when they’re most vulnerable financially.

Social stigma layers on top. Some people feel embarrassed asking basic questions about a phone or a computer. Nobody wants to feel like the only person in the room who doesn’t understand something everyone else takes for granted.

Why This Matters for Reentry

None of this is a footnote to reentry. It’s often the main event. A person can have every intention of finding work, staying in touch with family, managing their health, and still hit a wall because they can’t figure out how to reset a password or attach a file. That wall gets mistaken for a lack of effort or motivation, when really, it’s a lack of exposure. Nobody handed them a manual for the last decade of technology, because there isn’t one.

Programs that treat digital literacy as a side note are missing something core. It deserves the same weight as job training or housing assistance, because right now, it’s often the gatekeeper to both.

What Actually Helps

The good news: this is a solvable problem, and it doesn’t require reinventing anything.

Start with the basics, without judgment. Teach what a browser is, how to create and manage an email account, how touchscreens work. Skip nothing. Assume nothing. The person in front of you might have missed the entire smartphone era, and that’s not a knock on their intelligence.

Build hands-on practice into every session. Reading about how to fill out a job application isn’t the same as doing it with someone next to you who can answer questions in real time. Let people make mistakes in a low-stakes setting before they’re doing it alone under pressure.

Partner with libraries. Public libraries already run free tech classes and offer computer access. They’re an underused resource, and most reentry organizations don’t have to build this infrastructure themselves when it already exists a few blocks away.

Provide devices when you can, and Wi-Fi access too. A person can’t practice what they don’t have access to. Even short-term phone loans or a designated computer lab in your office can shift someone from stuck to moving.

Teach scam awareness directly. Cover phishing, fake job postings, and predatory lending apps as their own topic, not an afterthought. This protects people during one of the most financially fragile stretches of their life.

Recruit peer mentors. Someone who came home two years ago and has since figured out the basics can teach in a way that feels human, not clinical. Peer-led tech support builds trust faster than any formal class.

Normalize the learning curve. Say it out loud: “A lot changed while you were away, and that’s expected, not something to be ashamed of.” That one sentence can lower the wall enough for someone to actually ask a question.

Technology access isn’t a nice-to-have tacked onto reentry services. It’s the front door to almost everything else: work, housing, healthcare, staying connected to people who matter. When we treat digital literacy as essential and teach it with patience instead of assumption, we give people a real shot at catching up to a world that never stopped moving without them.

That’s how LINC and other reentry programs are meeting people where they are, and helping them get where they’re going.