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Immigration detention is formally not a punishment, but governments do use it to deter illegal residence. This study examines whether and how immigration detention affects detainees’ decision-making processes regarding departure, thereby possibly resulting in de facto “specific deterrence.” Semistructured face-to-face interviews were conducted in the Netherlands with 81 immigration detainees, and their case files were examined. Evidence is found for a limited, selective deterrence effect at the level of detainee's attitudes: most respondents considered immigration detention a painful and distressing experience, but only a minority—mostly labor migrants without family ties in the Netherlands—developed a preference to return to their country of citizenship in hopes of ending their exposure, including repeated exposure, to the detention. In line with defiance theory, we find that eventual deterrent effects mostly occurred among detainees who also attributed some measure of legitimacy to their detention. Among some detainees, the detention experience resulted in a preference to migrate to a neighboring European country.