Digital Literacy in Prisons: Preparing for Reentry In The Age Of Technology July 7, 2025 Digital literacy in prisons is essential for successful reentry. Learn how The Last Mile is transforming prison education and closing the digital divide for Justice Impacted People. Digital literacy in prisons is a crucial and urgent topic in the landscape of justice reform. In a world driven by cloud computing, QR codes, and AI-powered tools, most incarcerated Americans remain completely disconnected. While society races forward, they are locked out of the digital world, sometimes for years, even decades. This lack of access compounds the barriers justice-impacted individuals already face. Without training, even tasks like applying for a job or checking in at a medical appointment can become insurmountable. Without digital literacy, individuals reenter society digitally blind. This creates consequences not only for them, but for the communities to which they return. Modern Life Requires Digital Literacy Digital literacy is the ability to utilize information and communication technologies to locate, assess, create, and convey information. This technological skill set has become a foundational skill in surviving modern life. Accessing healthcare, applying for jobs, managing finances, and communicating with loved ones all require a degree of digital fluency. Today, over 70% of U.S. jobs require a medium to high level of digital skill. Yet, many returning citizens have never used modern tools like Google Docs, videochat, or online application portals. For most returning citizens, this skills gap becomes an immediate barrier. They struggle to access employment, housing, and even basic communication platforms, often leading to higher levels of recidivism. The Challenge of Reentry Into A Digital World Without structured preparation, the transition from prison to smartphones, cloud apps, and digital portals is a harrowing process. It’s immediate, jarring, and often overwhelming. Dr. Jane Hwang, research fellow at the Justice Health Research Program at UNSW Sydney, has studied digital exclusion among older Australians leaving prison. While her research focuses on Australia, the themes strongly echo realities in the U.S. Her study found that older justice-involved individuals felt like “strangers in a foreign world” upon release. Using public transit apps or checking in at health clinics became overwhelming challenges for the older individuals in her study. “Reintegration is really about finding your place again, connecting with people, managing your health, handling daily tasks, and building a sense of belonging. Without digital literacy, all of these things become much harder. If you can’t access health care, apply for jobs, or even stay in touch with family and support networks because those things now happen online, you’re left feeling isolated and overwhelmed.” Dr Jane Hwang, Research Fellow, UNSW Sydney Robert Chambers is an alumni and currently Academic Success Representative with The Last Mile. Despite his deep engagement with digital concepts inside, his first days after release felt chaotic. “Notifications were coming from every direction. I was flooded with account creations, password creations, new logins to apps and websites,” he recalled. “It was an unbelievable assault while I was trying to get my footing”. Dr. Hwang’s research supports this testimony. “When someone feels unable to manage everyday technology, it can really undermine their self-esteem. It can reinforce feelings of stigma or not belonging,” Dr. Hwang told us. “This sense of inadequacy can make people reluctant to seek help or engage with services. It sometimes leads to further social withdrawal.” Breaking Down The Digital Divide In Prisons Most U.S. prisons restrict or ban access to internet-connected devices. Even educational programming often relies on closed systems or outdated materials. These legacy prison programs fail to reflect the realities of today’s tech landscape. Brett Buskirk is an alumnus and Platform Systems Engineer with The Last Mile. Brett explains entering prison and seeing the divide first hand: “At first, it was like going backwards in time. You could go to the law library and they had typewriters. Not word processors, but old school devices that put paper into.” Over the past decade, The Last Mile has helped reshape what’s possible for digital access behind prison walls. Since its founding, TLM has worked to bridge the digital divide in prison by designing innovative, secure, and scalable educational programs tailored to a disconnected environment: 2010 — TLM launched in San Quentin as an entrepreneurship program, using analog tools to teach tech-based business concepts. 2014 — TLM launched the first computer coding program in a U.S. prison without internet access, using a custom-built, simulated coding environment. 2016 — TLM Works, a fully functional web development shop inside San Quentin, launched to provide real paid experience for students post-graduation. 2017–2022 — TLM expanded into new states and facilities, launching remote instruction, secure help desk support, and real-world client work through in-prison ventures. 2022 — TLM introduced a personal laptop pilot program, revolutionizing the learning experience and creating continuity between classroom and independent study. 2023–2025 — TLM’s digital curriculum and delivery model scale nationally, forming new partnerships to serve a growing network of incarcerated learners. This ongoing work continues to change what’s possible inside correctional facilities—paving the way for true digital inclusion and job readiness. Building Skills That Matter for Life After Prison Justice-impacted individuals who lack tech fluency are more likely to struggle with job applications, communication, and navigation of essential services. This disadvantage prolongs job searches and exacerbates economic instability, both of which are key contributors to recidivism. Perry Garner, an alumni and currently Social Media Coordinator with The Last Mile, described the contrast between prison and release: “You come out, and suddenly everything’s a screen. You need a password for a job application. You need a QR code to get into a building, and you’ve never even owned a smartphone.” “I see digital literacy as both a public health and a human rights issue. Without these skills, they’re essentially locked out of accessing the care and support they need in a society that’s become so reliant on technology.” Dr Jane Hwang, Research Fellow, UNSW Sydney Dr. Hwang explained the issue further: “There isn’t direct research showing that digital exclusion alone causes someone to go back to prison, but what we do know from studies on reintegration is that digital skills are now crucial to rebuilding your life after release”. So what are those digital skills that matter most after incarceration? Based on what programs like The Last Mile and others have seen in the field, here are just a few: Navigating job application platforms and uploading resumes Using email, messaging apps, and calendar tools Completing online forms for housing, healthcare, and IDs Participating in video calls and digital interviews Managing passwords, authentications, and app logins Accessing public services like transportation or benefits through apps Understanding online privacy, scams, and secure browsing basics These skills are essential tools for independent living, employment, and maintaining human connection in today’s digital-first society. What Happens When People Are Given Access When justice-impacted individuals are given the opportunity to develop digital literacy while incarcerated, their transitions into society can be significantly more stable. The Last Mile’s alumni stories offer powerful evidence of this impact. Perry Garner credited his smoother reentry to the preparation he received through The Last Mile. “I felt like I had a head start,” he shared. “I had a lot of the basic knowledge of how to navigate the digital world because of the training I had inside”. This digital readiness helped him avoid the disorientation many returning citizens face when confronted with app-driven systems, touchscreens, and digital forms. Johnson Thieu, an alumni and Senior Remote Instructor with The Last Mile, echoed a similar experience. He explained that without the opportunities he had, including working as a Braille transcriber and joining The Last Mile, he wouldn’t have been confident using modern systems. “If it wasn’t for The Last Mile, I would not have been able to become comfortable working with systems or computer applications, or software”. With all alumni from The Last Mile, digital literacy has proven to be a pathway for reclaiming agency. And in many cases, it is the difference between surviving after release and truly thriving. “The best time to introduce digital literacy is definitely while someone is still inside prison. It’s a more stable environment, and they actually have the time and space to focus. Once someone gets out, life can be incredibly hectic and overwhelming, so “it’s much harder to engage with any kind of training or support then.” Dr Jane Hwang, Research Fellow, UNSW Sydney Designing a Future That Includes Everyone Looking ahead, the implications of digital literacy in prisons go far beyond reentry. Programs that prioritize digital fluency reduce violence inside facilities, lower recidivism, and foster safer, more stable communities. Controlled digital access and structured education offer a stronger return on investment than punitive surveillance or isolation-based models. This belief is echoed by TLM alumni who experienced firsthand what it means to have—or be denied—that opportunity. Perry Garner put it simply: “There’s so many guys that never had an opportunity to do anything. If I didn’t get into TLM and I didn’t go to San Quentin, I probably wouldn’t be sitting here right now.” Robert Chambers, reflecting on the advantages he had in his reentry, emphasized the urgency of expanding access: “I had a lot of help and a lot of handholding, but I realize how incredibly fortunate I was… There are people who are just as smart and just as determined who simply never got that chance. That’s who we need to reach next.” The Future of Digital Literacy in Prisons The Last Mile is building the next chapter in justice-centered education—and it starts with a bold, future-ready curriculum designed to turn digital literacy into a true career accelerator. Set to launch in early 2026, this national model will equip people in prisons across the United States with the professional fluency, technical skills, and cultural tools they need to thrive in the digital economy from day one after release. This new curriculum is designed not only to address the existing digital divide but to anticipate the future of work. In an era where automation and artificial intelligence are rapidly changing employment landscapes, The Last Mile is focusing on skills that won’t be easily replaced by AI. These include communication, creative problem-solving, systems thinking, project coordination, and entrepreneurship—roles that rely on human insight and adaptability. The curriculum also integrates soft skills training, time management, professional etiquette, and job search strategy. Participants will engage in a progressive, layered learning experience that combines core digital literacy with high-impact tools like Google Workspace, HTML, email systems, and remote collaboration platforms. Just as importantly, students will practice real-world decision-making using simulators provided by partners like Stukent, which replicate the experience of working with common apps, websites, and business systems. These tools offer a safe, secure environment to build confidence, context, and capability before reentry. Closing The Digital Literacy Divide In Prisons The Last Mile’s new programming will launch at one of our most ambitious facilities to date: San Quentin, which is currently undergoing a transformation into a Level 2 Rehabilitation Center as part of the California Model. Set to open in 2026, its newly constructed education wing will house one of the largest TLM classrooms in the country—and will serve as a national flagship for what’s possible when justice reform is rooted in education, technology, and opportunity. The Last Mile’s expansion in San Quentin will also mark the start of something even bigger. For the first time, The Last Mile is introducing a remote learning platform that allows other organizations to deliver their own curriculums inside correctional facilities. This represents a monumental shift: incarcerated learners will gain access to a wide range of high-quality programming—delivered securely, remotely, and interactively—through technology that has never before been available in U.S. prisons. This platform is the foundation for a scalable, replicable model of digital-first prison education. One that brings in partners, unlocks new content, and breaks the monopoly of outdated, one-size-fits-all systems. The work happening through The Last Mile shows what’s possible. Now it’s time for Departments of Correction across the country to join in. By closing the digital gap, we can open up an entire ecosystem of opportunity behind the walls. Without structured and relevant digital education, justice-impacted individuals are left to navigate a fast-moving, tech-driven society with no preparation. Digital literacy in prisons is no longer optional—it is the baseline for a stable, productive life post-incarceration. By Robert Roche, VP of Marketing at The Last Mile. Want articles like this one in your inbox? Subscribe to The Last Mile Marker, a newsletter offering in-depth insights, critical updates, and inspiring stories on criminal justice reform and second chances.