While free world society has a burgeoning reliance on technological access to legal platforms for both civil and criminal procedure, prisoners have little capacity to engage with computers and are typically banned from online legal sources. At the same time, the technologising of criminal procedure through the high uptake of audio visual links has seen the rapid decline of physical visits by lawyers to prisoners. Prisoners have limited reciprocal powers to demand technological access to the external world and must rely on largely obsolete forms of communication. In an era where legal resources are increasingly digital, can the continuing asymmetrical restrictions on prisoners’ access to technologies be justified? This article analyses recent Australian case law to understand the challenges presented for prisoners in the preparation of their legal proceedings.