A long standing debate has existed between those who believe deterrence-based enforcement strategies work for gaining compliance from offenders and those who believe gentle persuasion and cooperation is more effective. This article is concerned with the issue of how to best deal with offenders so as to increase support for the law and lower the rate of subsequent re-offending. Using survey data from 652 taxpayers who have been through an enforcement experience with the Australian Taxation Office, the present study will show that depending on how an enforcement experience is perceived by offenders (as either stigmatic or reintegrative in nature) can influence the feelings of resentment they experience, but more importantly these feelings of resentment mediate the effect of punishment on subsequent compliance behaviour. In other words, it is these feelings of resentment in response to disapproval that go on to predict who will and will not comply with their subsequent obligations under the law.