The technological development of nuclear and digital power emerged after World War II in such a way as to raise new questions about the extent to which technologies are complimentary to human life. Even though technologies, from the plow to the pencil, have been cultural phenomenon since the beginning of human civilization, recent questions are more specifically about the ethics of technology with a particular attention to its proper use. This paper has two aims: first, to consider historical narrations that makes our cultural moment distinct; and second, to consider alternative modes of evaluating proper technological use. This paper will first engage with historical accounts of technology, primarily in conversation with Jacque Ellul and Ivan Illich, in order to show how our modern technologies, differ from previous centuries, and how we might reassess our understanding of the conviviality of technology. Next, this paper will engage with St. Augustine in order to offer a theological account of technological use according to his idea of “fittingness,” or what is proper to human life. Contemporary standards for technology tend to affirm anything that “works.” Such accounts, however, leave us with a diluted framework for judgement. Augustine provides a richer conceptual outlook when he describes fittingness: given the assumption that God designed an orderly world, everything has a “fitting” use. Thus, success (what “works”) is not and should not be the measure for “rightness.” Instead, “fittingness,” according to Augustine and “conviviality,” according to Illich, are more humane paradigms for prudential judgment of technology.