Structurally, professional pedagogy has to deal with paradoxical tensions. These unsolvable tensions have no easy solutions, but have to be dealt with reflexively. This article reconstructs the complexification of paradoxes of socio-pedagogical action in times of securitization on the basis of observation and interview data gained in the field of prevention and deradicalization in German prisons. We demonstrate the influence of securitization on the paradoxical tension between the principles of pedagogy and social work and the logics of prevention and prison, and on the tension between being close and being distant in pedagogical interaction and relationships. We show to what extent the dilemmas of pedagogy are interrelated: one-sided solutions in one aspect can eventually spill over to other dilemma constellations.