Background: Although research has identified a wide range of risk factors for suicidal behaviour in prisoners, it does not establish who is most likely to act on their suicidal thoughts while incarcerated. Aim: To examine which clinical, criminological, and custodial factors are associated with suicidal ideation and the transition to suicide attempt in prison. Methods: Data were collected from a random sample of 1203 adult men incarcerated across 15 prisons in Belgium, who represent 12% of all male prisoners nationwide. Results: One-third (33%) of participants reported having suicidal thoughts during their incarceration, of whom 26% attempted suicide in prison (9% of all prisoners). Factors independently associated with suicide attempt among prisoners with suicidal ideation were violent offending (aOR = 2.64, 95% CI 1.33–5.23), in-prison drug use (aOR = 2.30, 95% CI 1.25–4.22), exposure to suicidal behaviour (aOR = 1.96, 95% CI 1.04–3.68), and a history of non-suicidal self-injury (aOR = 1.90, 95% CI 1.08–3.36). Whilst related to suicidal thoughts, markers of psychiatric morbidity and aspects of the prison regime were not associated with the progression to suicide attempt. Limitations: The findings were based on cross-sectional data derived from self-report measures. Conclusions: Many prisoners who think about suicide do not attempt suicide while incarcerated. Factors associated with suicidal ideation are distinct from those that govern the transition to suicidal behaviour. Longitudinal data are needed to confirm whether the identified factors predict behavioural enaction during the course of imprisonment.