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This paper examines perceptions of risk around hiring people with convictions(s) (PWCs) in Ireland. Employment remains a key protective factor on the desistance journey and supports the development of an inclusive, fair, and equal society (Carr et al., 2015; Healy, 2017; Reich, 2017). While there is evidence that employers are broadly open to hiring PWCs, they raise concerns based on perceptions of risk. The precise definition what constitutes risk, or a ‘risky’ applicant, was not clear across the dataset. Employer participants reported various potential concerns about employing PWC while PWC participants’ experiences of being deemed a risk were often vague and undefined. Safeguarding staff and/or clients or customers was the primary consideration of the employer participants. Conversely, the risk facing PWCs in disclosing their history is not discussed by employers. Trust is often offered conditionally and PWC participants feel that they must achieve impossibly high thresholds to overcome presumptuous risky subjectivities. The absence of guidance and uncertainty about evidence-based approaches and legal requirements leads to inconsistent policies and practices while PWCs continue to face intersecting barriers to employment and reintegration. This paper draws on a multi–method study of employers’ attitudes to hiring PWCs and experiences of employment pathways for PWCs.