New information and communication technologies (ICTs), such as cell phones, email, and social media, have been transforming how social movements recruit, organize, participate in collective action, and experience repression. Yet, limited scholarship has addressed the uses of these technologies by social movements organizing within American prisons. Using a dialectical interpretive approach, I examine how a coalition of prisoners’ rights organizations uses ICTs to plan and participate in collective resistance across prison walls. The coalition, referred to here as the New Prisoners’ Rights Coalition (NPRC), organizes against low and no-wage prison labor, unhealthy and unsafe prison conditions, and inhumane prisoner treatment. The NPRC has a multi-platform public digital presence and mobilizes prisoner activists and free activists. Through narrative description, I summarize the ways NPRC activists use ICTs from December 2013 through September 2016, noting changes in ICT use over time and in response to movement repression. I find that new ICTs offer innovative ways for NPRC activists to record and document their environments, communicate privately, and communicate publicly. ICTs, however, do not remove all barriers to activism or ensure that activists’ concerns are resolved or even taken seriously. NPRC activists struggle to overcome stigma and mischaracterization online. They face physical repression, interpersonal hostilities, institutional sanctions, economic repression, legal sanctions, interpretive repression, surveillance, and monitoring. In different circumstances, the NPRC responds to repression by increasing ICT use, decreasing ICT use, going dark, migrating from one online platform to another, and shifting digital responsibilities from prisoner activists to free activists. I explain how, most of the time, the digital unreachability of the prison environment makes it difficult for NPRC activists to substantiate their claims of mistreatment, abuse, and injustice. Moreover, I consider how current prison technology policies may be inadvertently pushing NPRC activists into difficult-to-monitor online spaces and exacerbating safety concerns of corrections workers.