The idea of using artificial intelligence as a support system in the sentencing process has attracted increasing attention. For instance, it has been suggested that machine learning algorithms may help in curbing problems concerning inter-judge sentencing disparity. The purpose of the present article is to examine the merits of this possibility. It is argued that, insofar as the unfairness of sentencing disparity is held to reflect a retributivist view of proportionality, it is not necessarily the case that increasing inter-judge uniformity (...) in sentencing is desirable. More generally, it is shown that the idea of introducing machine learning algorithms, that produce sentencing predictions on the ground of a dataset that is built of previous sentencing decisions, faces serious problems if there exists a discrepancy between actual sentencing practice and the sentences that are ideally desirable. (shrink)