The “pains” of having a sexual conviction have been cited by Ievins (2022; 2023) in their work on the society of ‘sex offenders’ and the stains of imprisonment. Indeed, much work exists analysing the situated experiences of men navigating life with a sexual conviction in prison (Blagden et al., 2019; Ievins and Crewe, 2015) and to an extent, in the community (McCartan and Richards, 2021; Saunders, 2020; Teague, 2022). Whilst such literature is critical for understanding some of the broader lived realities of those who have a sexual conviction, there is a paucity of understanding on the nature and impact of more nuanced aspects of living with a criminal conviction for a sexual crime. One such area in particular relates to ‘disclosure’, the process of disclosing criminal record history to another individual, organisation, or in a particular forum. Interestingly, the notion and process of disclosure in regard to individuals who have a sexual conviction has not been subject to critical appraisal encompassing the totality of what it entails, to whom, and in what context. Instead, much information and literature around disclosure centres around necessary, but practically oriented, guides relating to when, and how, to disclose in the process of applying for jobs, college, or university (see for example: Nacro, 2023; Unlock, 2023). This chapter utilises psychosocial theory to critique (i) the socio-legal landscape surrounding disclosure; (ii) the period before disclosing—‘anticipatory disclosure’; and (iii) the impacts of disclosing a conviction for a sexual offence. To do this, the chapter sets out the realities of resettlement before conceptualising ‘anticipatory disclosure’. Following this, the chapter subsequently develops a critical discussion around the implications emergent from such conceptualisation, and recommendations for policy and practice.