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Our prior work has identified a trade-off that new entrants face in obtaining favorable market reception, whereby initial entrants suffer from a deficit of legitimacy whereas later entrants suffer from a deficit of authenticity. This research has also proposed that a single mechanism is responsible for this trade-off: the tendency for customers and other stakeholders to assess the entrant's claim to originality based on the visible work that it has done to legitimate the new product or organizational form. This chapter extends and deepens our understanding of such “legitimation work” by showing how it can illuminate cases that seem in the first instance to defy this trade-off. In particular, we focus on two “off-diagonal” cases: (a) when, as in the case of “patent trolls” and fraudulent innovators, early entrants are viewed as inauthentic despite having a credible claim to originality; (b) when late entrants, as in the case of Dell Computers, mechanical watches and baseball ballparks, are viewed as authentic despite obviously not being the originators. We clarify how each off-diagonal case represents an ‘exception that proves the rule’ whereby audiences attribute authenticity on the basis of legitimation work rather than on the order of entry per se. The last case also leads to an opportunity to clarify why “cultural appropriation” can sometimes project authenticity and sometimes inauthenticity, why audiences bother to make inferences about a producer's authenticity on the basis of visible legitimation work, and why legitimacy is a universal goal of early movers whereas authenticity varies in its importance.