Inside the Rise of Remote Learning in Prisons: How The Last Mile is Redefining Correctional Education April 14, 2025 Remote learning in prisons presents a seismic shift in how we think about justice, education, and opportunity. The Last Mile is pioneering this model, proving that when you unlock access to digital education, you unlock human potential. Remote Instruction: A New Era of Prison Education When TLM co-founder Chris Redlitz walked into San Quentin in 2010, the idea of teaching software development behind bars was virtually unthinkable. “Everything was analog,” Chris remembers. “They wrote their business plans by hand. There were no computers, no internet. The concept of remote learning was so foreign, it didn’t even feel like a moonshot—it felt impossible.” Fast forward to today: TLM operates in 16 facilities across 8 states, with a secure, cloud-based Learning Management System (LMS) powering instruction in web development, audio/video production, and soon, project management and enterprise sales. “We realized early on that if we were going to scale, we needed technology,” said Chris. “But our philosophy was always people first, technology second. Remote instruction wasn’t just about plugging in laptops—it required a just change in mindset.” Introducing remote learning into correctional environments came with major cultural and logistical hurdles. “Convincing the Department of Corrections that remote instruction was both safe and effective took years,” Chris explained. “We had to prove that it was secure, that it worked, and that it wouldn’t compromise institutional integrity.” TLM’s platform records every class, uses closed networks, and is fully audit-friendly. It was a massive leap of faith for corrections departments—but it worked. The model has been validated, expanded, and now shapes national conversations around prison education. What Remote Learning Means to TLM Students Henry Dillard, a TLM alum who spent 25 years incarcerated, recalls his first days in the tech classroom. “It was a whole new world. I hadn’t seen a computer since the floppy disk days. I was intimidated,” he says. “But remote learning helped me realize I could learn in new ways. It changed how I saw myself.” Henry went from unsure student to in-class instructor, eventually becoming a remote learning manager. “Helping others through the same journey I went on made me understand the power of peer teaching. You start to believe in yourself when others are learning from you.” Remote instruction creates a unique environment in prison—one where students connect with instructors beyond the walls. “It was so humanizing to have people speak to us by name, to treat us like professionals,” Henry shared. “You don’t feel like a number anymore—you feel like a person.” The data backs up what Henry experienced firsthand. According to The Last Mile’s 2024 Annual Report, students in TLM’s remote learning classrooms are gaining in-demand skills in web development, audio/video production, and game programming—fields designed to align with real employment opportunities upon release. The results are undeniable: only 5% of TLM alumni have been reincarcerated for new offenses, and 75% of those who’ve been released for six months or more are now employed. These numbers are transformative, and they prove that the model works. When justice-impacted individuals are given access to quality education and treated with dignity, they thrive. Changing the Mindset Inside Prisons With Innovative Technology Executive Director Kevin McCracken emphasized how remote instruction impacts the culture inside correctional facilities. “You see men and women walk into the classroom expecting another program that won’t lead anywhere,” Kevin said. “But within weeks, they’re asking questions, staying after class, and mentoring each other. It creates a ripple effect that shifts the whole atmosphere inside the prison.” But that shift doesn’t happen by accident. It’s intentional—and deeply rooted in TLM’s philosophy of human-centered education. Kevin explained, “We’re creating an environment that builds confidence, connection, and community. When students realize this is their classroom, that it’s built for them and powered by people who believe in them, it unlocks something that’s been dormant for a long time.” That’s where remote instruction becomes a catalyst for growth: The digital format allows students to engage with industry professionals, alumni, and instructors from outside the prison walls. This exposure broadens their view of what’s possible and introduces new role models. Kevin is quick to point out that TLM’s success isn’t about tech alone. “You can’t just throw laptops at the problem,” he said. “We’ve created a structure of accountability, peer mentorship, and instructor support that helps people see their own value. That transformation—that shift in identity—is what reduces recidivism.” With students now returning as teaching assistants, and alumni stepping into remote instructor roles, Kevin believes the model is proof that the future of education in prisons must be scalable, sustainable, and rooted in dignity. “What we do isn’t about charity or handouts. It’s about giving people the tools and structure to build something real,” he said. “That transformation—that shift in identity—is what reduces recidivism.” Scaling The San Quentin Rehabilitation Center and Beyond In January 2026, TLM’s redesigned classrooms will open at the reimagined San Quentin Rehabilitation Center. This facility represents the next chapter of remote learning in prisons—one that fuses state-of-the-art technology with The Last Mile’s people-first ethos. The classrooms will be outfitted with smart boards, secure video conferencing, and modular workstations. But beyond the tech, the focus is on fostering professional norms. “We’re creating a space that feels like a startup office, and not a prison classroom,” said Kevin McCracken. “When you shift the environment, you shift behavior. Students start thinking differently about what’s possible.” But the impact of this new model goes far beyond San Quentin. In 2026, TLM will make its secure remote learning technology—delivered through its Platform-as-a-Service (PaaS) model—available to other organizations across the country. This opens the door for a broader range of remote learning providers to bring their courses into correctional facilities for the first time. Whether it’s digital design, sales training, or data analysis, justice-impacted learners will have access to a wider array of high-quality education programs than ever before. At the same time, TLM students will begin using this same technology to participate in remote internships, interviews, and even paid employment while incarcerated. By connecting students to real companies through secure, work-ready infrastructure, TLM is building a bridge from the classroom directly to the workforce—before release. This integration of education and employment within prisons will give students the ability to hone their skills in real-world environments, build professional relationships, and enter the job market with relevant experience already under their belt. Why Remote Learning Is the Future of Prison Programming Remote instruction succeeds where other prison education programs struggle because it doesn’t just digitize learning—it humanizes it. “Our instructors are mentors as well as experts,” said Chris Redlitz. “Many are graduates of our own program. We’re showing that justice-impacted individuals aren’t just capable of growth—they’re becoming essential to running the system from within the prisons.” TLM’s model blends real-time instruction, self-paced modules, and a culture of peer mentorship and accountability. Students build portfolios, earn industry credentials, and leave prison with the skills needed to succeed in competitive roles. As prison systems across the country face staffing shortages, budget cuts, and growing pressure to reduce recidivism, TLM’s remote instruction model offers a clear, cost-effective, and scalable solution. Remote learning in prisons is the blueprint for the future of correctional education. By combining secure technology, scalable systems, and a relentless belief in human potential, The Last Mile is proving that transformation is not only possible—it’s happening. And we’re just getting started. By Robert Roche, VP Of Marketing at The Last Mile. Want articles like this one in your inbox? 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