Critical prison studies have demonstrated how states use imprisonment and detention not only to punish individuals, but also to quell dissent and disrupt opposition movements. In protracted conflicts, however, the use of mass incarceration and unlawful detention often backfires on states as politically motivated prisoners exert their relevance by making imprisonment itself a central issue in the wider conflicts. Rather than retreating to the margins, prisoners have taken back prison spaces as loci of resistance, forcing both state authorities and their own external parties to engage with them seriously as political actors. This subversion of the prison space is not automatic, however; as this article demonstrates, prisoners have exerted the most influence on both authorities and their own factions when they have combined pragmatism and radicalism through multilevel strategies such as establishing praxes for self-education and organizing; using everyday non-compliance to challenge prison administrators; and occasionally, engaging in hunger strikes that exert boomerang pressure from external factions and solidarity networks on state authorities. Drawing from the case studies of Israel–Palestine, Northern Ireland and South Africa, this research shows how these radically pragmatic tactics create a ‘trialectic’ interaction between prisoners, state authorities and external networks, forcing direct and indirect negotiations regarding prisoners’ rights, and, at times, influencing broader conflict dynamics