Strategy blindness is commonly understood as an unexpected outcome of IS strategy implementation that results as users make sense of new IT resources in unintended ways. What could be learned by instead treating strategy blindness expected? To this end, this paper unpacks some common assumptions of strategic failure and presents an alternative assumption ground. To explain how masculinites form sources of strategy failure, I reanalyze IT use at a Swedish paper-mill as negotiated among rough and respectable men: blue-collar workers and white-collar managers are shown to maintain distinct hierarchies yet enact the same fixed IT use reality, in each case, intimate relations to the paper machine dictated their ways. Power plays of optimization and mastery illustrate each identity. I then critique current ideas in strategic management and received notions of how IT matters in strategy practice.