For entrepreneurs, establishing and maintaining new venture legitimacy is a complex endeavor. Various factors complicate this process, including issues of optimal distinctiveness, audience diversity, market category evolution, and multiple legitimacy thresholds. Moreover, the establishment and maintenance of new venture legitimacy is an intricate process that unfolds over time. In this essay, I review and integrate prior work on new venture legitimacy not only to highlight these complications, but also to consolidate insights, theoretical nuances, and empirical observations to describe what happens when entrepreneurs confront multiple complications at the same time. In so doing, I propose that configurational approaches provide a valuable theoretical perspective to enhance knowledge related to new venture legitimacy. I also highlight exemplar studies that have adopted these perspectives, accounting for multiple new venture legitimacy complications in a single analysis. This provides a basis to understand recent advances in the new venture legitimacy literature, and inspires and opens up new research opportunities for further exploration.