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In today’s digital world, access to and proficiency in digital technologies are essential. However, formerly incarcerated individuals often face significant challenges due to digital disconnection during incarceration, making it harder to navigate reentry tasks such as finding housing, employment, or healthcare. Research highlights the negative impact of this digital deprivation, prompting scholars to explore solutions like the "digital rehabilitation model" (Authors, 2018). This model suggests that providing digital tools and skills training during and after incarceration can ease reentry and improve rehabilitation outcomes. While recent studies focus on the experiences of incarcerated individuals, there is limited research on how prison staff and administrators perceive digital technologies in carceral institutions. Their perspectives are crucial, as they influence whether and how digital access is integrated into carceral settings. Understanding their viewpoints helps identify opportunities for digital inclusion and barriers preventing widespread adoption. To address this gap, Authors (2023) developed the (Blinded for peer review)™ tool, which assesses the digital maturity of correctional institutions. Digital maturity refers to an organization’s capacity and willingness to implement and sustain digital solutions. The tool evaluates five dimensions: incarcerated people-centric technologies, organizational structures, culture, existing capabilities, and progress evaluation. Combining qualitative case studies and quantitative data, it examines if and how prisons implement digital access and training. This article applies the digital rehabilitation model to assess digital maturity in prisons worldwide. Through case studies from Europe, Asia, and Oceania, it explores two key questions: (1) What is the current state of digital rehabilitation efforts? (2) What barriers hinder digital maturity in prisons? The paper reviews relevant literature, discusses methodologies, analyzes case studies, and highlights practical challenges such as funding and infrastructure limitations.