In this paper, I argue for the counter-intuitive conclusion that the same adaptive preference can be both prudentially good and prudentially bad for its holder: that is, it can be prudentially objectionable from one temporal perspective, but prudentially unobjectionable from another. Given the possibility of transformative experiences, there is an important sense in which even worrisome adaptive preferences can be prudentially good for us. That is, if transformative experiences lead us to develop adaptive preferences, then their objects can become prudentially better for our actual selves than the objects of their non-adaptive alternatives would now be. I also argue, however, that the same worrisome adaptive preferences might still be prospectively prudentially objectionable: that is, our pre-transformation selves might be prudentially better off undergoing a non-adaptive alternative transformative experience instead. I argue that both claims hold across the range of the most broadly-defended accounts of well-being in the literature.