The practice of strategic enrollment management (SEM) can be likened to navigating a ship through uncharted waters. Dating back to the 1970s, the very concept of enrollment management came into being and has since evolved in the face of a steady progression of daunting challenges requiring repeated course corrections. A massive demographic downturn in the early 1980s was followed closely by a sea change in the funding hydraulics in higher education, punctuated by a significant drop in public funding. While many institutions regained their enrollment equilibrium in the latter half of the 1990s, in the new millennium a fresh set of obstacles that threaten the well-being of not only the institutions, but American society as a whole has to be faced. The context in which SEM practitioners operate is changing again in ways that will forever alter how people do business as institutions of higher education. That context is made up of new or newly-evolving challenges related to demographics, economics, and institutional priorities. These issues have gained increased attention as observers contemplate the significant implications for the practice of SEM, institutional outcomes, and the long-term economic and social well-being of the United States. This paper highlights a few of the more prominent enrollment challenges currently faced by colleges and universities, and concludes with summative comments about the implications of those challenges for the practice of SEM. (Contains 5 figures.)