Recent years have seen a surge of interest in the question of whether humans should reproduce. Some say human life is too punishing and cruel to impose upon an innocent. Others hold that such harms do not undermine the great and possibly unique value of human life. Tracing these outlooks historically in the debate has barely begun. What might philosophers have said, or what did they say, about human life itself and its value to merit reproduction? Herein it is useful to look to Kant, who wrote much on whether, by reproducing, humans do wrong or right morally. Two main arguments are put forward and assessed: one examining whether perfect or imperfect duties condone reproduction, the other whether Kant’s teleological or, in the opposite sense, his eschatological outlooks can salvage reproduction. These two arguments are essential for building the entire argument. I find that, although Kant’s arguments against reproducing are strong, some of his writing seems to support reproduction as a good. Yet, must we assume an author, even one who strove for systematicity, is consistent over an entire life’s work on every issue, especially if it is not handled directly in a single work? I conclude that Kant does not sufficiently, systematically support anti-natalism as more moral than pro-natalism. It is best for the current debate to grapple with the very dilemma that daunted Kant.