This contribution examines the relationship between automation, discretion, and proportionality. It argues that automation efforts in public administration need to be further discussed and analyzed in relation to requirements of proportionality flowing from both national and European law, as the principle carries important implications for both the implementation of automated systems and the responsibilities of decision-makers within those systems. The different facets of proportionality flowing from, inter alia, constitutional, and human rights law, administrative law, and data protection law are explored, with four distinct stages of proportionality analysis identified: legislative, system, decision, and ex post proportionality. These stages all carry different implications for discretion and the prospects of automation. Through the requirements in these different stages, the authors conclude that proportionality ought to act as another driver of keeping human oversight of automated systems. This human oversight will however, in relation to proportionality, require further contextual awareness and control of correct output proportionality, a role which may be significantly more demanding than a more limited oversight implied by current legal discussions on "humans in the loop".