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Young men in jail and prison are vulnerable regarding sexual health and the fulfilment of their sexual rights. As a response to this, the Swedish Association for Sexuality Education (RFSU) has been providing sex education to young, incarcerated men, via a project initiated by and in cooperation with the Swedish Prison and Probation Services (SPPS). This article is a qualitative exploration of how RFSU educators experienced their work, and of how staff within SPPS experienced the initiative. Eight RFSU educators, and six persons working within SPPS were interviewed, and a thematic analysis was conducted. Overall, the experiences described by RFSU educators and by SPPS staff were similar, they regarded sex education sensitive to what young men wanted to discuss as valuable and the project feasible. Future improvement areas include strategies on how to handle toxic masculinity among young men in jail and prison. Additionally his, the different aims that the organisations RFSU and SPPS have, and how young men navigate them, must be acknowledged. Young men’s voices are missing in this study, and examining their experiences of the sex education in future work would be valuable.