The study examines the association between the size of previous environmental sanction charges and subsequent compliance towards environmental regulations. Data used for the study come from about 9000 Swedish firms fined sometime between January 2002 and December 2012. Probabilities of compliance across various levels of sanctions are estimated using life-table methods and tested for equality using standard nonparametric methods. Association between size of sanction charges and subsequent behaviour is modelled by proportional hazard model for the rate of recidivism as well as by a family of flexible parametric accelerated failure-time models for the duration of compliance. The results show that duration of compliance may be described by a log-normal distribution. Further, it is demonstrated that sanctions charges do have significant detering effects on the risk of recidivism though the strength of the detering effect depends on whether or not we account for other possible correlates of recidivism. Possible explanations of the results and their policy implications are discussed; limitations of the current study highlighted; and potential extensions for future studies outlined.