Steady periods of budget surpluses can hide, and effectively defer attention being given to, systemic problems that only a fiscal squeeze can reveal. This is the situation that this article addresses. For the past quarter century, state tax administration has largely operated smoothly. But a problem with largely uninterrupted growth is that those processes that worked from year to year in the “good times” are not necessarily reliable for the “bad times.” Thus, the Great Recession did not as much create new problems for state tax administration as it exposed the challenges that already confronted the profession and now need attention. Taking a cue from the “tax gap” literature that administrators and academics often talk about, the article identifies seven major gaps that pose significant challenges to tax administration as the states address (or at least ought to address) in the postrecession years ahead.