The article presents a personal historical review of the person-organization fit (PO) literature by Amy Kristof-Brown, Benjamin Schneider and Rong Su. We present six conundrums and research evidence about each that we’ve encountered while studying fit during our careers: (1) What exactly is PO fit?—the term can be narrowly or broadly defined, but must be distinguished from other forms of Person-Environment (PE) fit; (2) What is the best way to measure PO fit?—there are a variety of ways, each with strengths and liabilities and the measure of P and O can vary across a variety of attributes; (3) At what level of analysis is PO fit?—although conceptually cross-level, it has been studied most frequently as an individual-level variable; (4) To what extent does PO fit actually matter?—quite a bit, especially with regard to individual attitudes and turnover, but there are many caveats including measures and national culture; (5) Is PO fit always desirable? — for individuals generally yes, but there can be benefits of misfit; for organizations the answer is still unknown, particularly with regard to diversity; and (6) What are the implications of PO fit change over time?—it is clear that people engage in purposeful activity toward establishing fit in their lives, and purposeful organizational tactics toward accomplishing productive fit is recommended. Addressing these conundrums, we provide thoughts on future directions for research on PO fit and practical implications for managers who want to maximize the benefits of PO fit.