<p>This essay is a contribution to a symposium on Adam Kolber’s Punishment for the Greater Good. As the title suggests, the essay focuses on the issues of punishment and regret. Its main thrust is a critique of Kolber’s failure to acknowledge the salience of retrospective normativity. This failure divorces Kolber’s attempt to justify punishment from our actual current carceral practices, which are fundamentally backward-looking responses to past (actual or supposed) wronging. It also limits Kolber’s ability to account for the normative reasons we have to regret these practices: mistaking regret as solely a matter of feeling and human psychology, while ignoring its backward-looking normative force.</p>