In this essay, I consider a particular version of the thesis that the blameworthy deserve to suffer, namely, that they deserve to feel guilty to the proper degree (a thesis I call "Desert-Guilt"). Two further theses have been thought to explicate and support the thesis, one that appeals to the non-instrumental goodness of the blameworthy receiving what they deserve (in this case, the experience of guilt), and the other that appeals to the idea that being blameworthy provides reason to promote the blameworthy receiving what they deserve (again, in this case, the experience of guilt). I call the first "Good-Guilt" and the second "Reason-Guilt.” I begin by exploring what I take to be the strongest argument for Good-Guilt which gains force from a comparison of guilt and grief, and the strongest argument against. I conclude that Good-Guilt might be true, but that even if it is, the strongest argument in favor of it fails to support it in a way that provides reason for the thesis that the blameworthy deserve to feel guilty. I then consider the hypothesis that Reason-Guilt might be true and might be the more fundamental principle, supporting both Good-Guilt and Desert-Guilt. I argue that it does not succeed, however, and instead propose a different principle, according to which being blameworthy does not by itself provide reason for promoting that the blameworthy get what they deserve, but that being blameworthy systematically does so in conjunction with particular kinds of background circumstances. Finally, I conclude that Desert-Guilt might yet be true, but that it does not clearly gain support from either Good-Guilt or Reason-Guilt.