Tannaitic discourse surrounding the biblical commandment to rebuke reveals early rabbinic anxiety over the effectiveness of reproof both as a general act and as a specific scriptural injunction.  In this paper I describe the ways through which the tannaitic midrash known as Sifre Devarim portrays potential negative outcomes from performances of reprimand, highlighting the pitfalls of the act of rebuke.  Based upon these early rabbinic statements I demonstrate how Sifre Devarim effectively circumvents or limits the biblical mandate itself.  In addition, I argue that in attempting to gain control over the practical fallout from rebuke and preventing the fulfillment of this verse, the tannaim simultaneously undermine their own authority.