The present study brings personality research into the realm of computer games. We used a novel method—the Prison Tycoon computer game—to explore participants’ attitudes toward rehabilitation and punishment. Forty-two men and 48 women were asked to construct a virtual prison equipped with rehabilitation, correction, and neutral facilities. Financial investment spent on each respective type of facility was treated as an indicator of a participant’s particular attitudes toward punishment. Additionally, participants completed the NEO Five-Factor Personality Inventory. Results indicated that Neuroticism and Openness to experience may be reliable predictors of one’s willingness to rehabilitate prisoners (measured as the amount of money spent on rehabilitation/correction facilities). This novel experimental method sheds new light on the issue of reliably and ecologically measuring attitudes in the lab and provides further evidence that computer games offer a new, effective alternative to classical research methods in this area.