The Minnesota Sex Offender Program (MSOP) offers treatment to sex offenders civilly confined after they complete their prison sentences. In this article, we enhance the notion of kairos in rhetorical situations with the perceptions of risk and the sociological concept of moral panic by tracing three kairotic moments involving MSOP: the 1992 Dennis Linehan civil commitment case; the 2003 murder of college student Dru Sjodin; and the 2012 provisional discharge of Clarence Opheim. We examine the political, public, and media response to these events and provide the results of 21 interviews with stakeholders. In doing so, we hope to illustrate how moral panic and risk perception can so influence what seems the right choice at the right time that stakeholders may get caught in what we call kairotic cycles, where solutions to a problem are stymied by competing perceptions and by entrenched positions that reoccur over time and without resolution.