Suicidal behavior among prisoners is a major problem. The objective of this study was to compare prisoners who have made an attempt at suicide vs non-attempters and further to compare single vs multiple suicide attempts. Among 1,537 prisoners, 200 (13%) had a lifetime history of attempting suicide and 92 (6%) had made multiple attempts. Those who had made multiple or single attempts were compared on socio-demographic, developmental, personality, forensic, and psychiatric variables. In a re-analysis we also compared non-attempters with attempters in this larger sample. The comparison showed that prisoners who had made multiple attempts had experienced significantly more childhood trauma, were more introverted, less resilient, had a history of self-mutilation, and had more suicidal ideation. Anger and hostility scores and criminal and violence histories significantly differentiated prisoners who had attempted from those who had never attempted but they did not differentiate multiple from single attempters. Having a history of multiple attempts may be indicative of more severe psychopathology in prisoners, as found in other populations. These findings may be helpful in predicting which prisoner is at increased risk of exhibiting suicidal behavior while incarcerated and after release.