To understand the experiences of leaders in student affairs in higher education and to document the strategies they used to cut budgets and the results of these actions, the authors conducted a qualitative research study using public institutions as case studies. Data were gathered in 2005 through phone interviews with senior student affairs officers (SSAOs) from 12 public colleges and universities to study the budget reductions that had occurred in the previous three to four years. After the recession hit in 2009, the researchers gathered additional data from the same institutions to determine if budget cuts were still a factor and if the strategies the SSAOs used and the results had changed over the ensuing four years. Several research questions were probed in both stages of the process: How have student affairs organizations used reduction, downsizing, and integration of units to respond to budget reductions? Did these factors change over time? What are the resulting changes in organizational structure, services, people, and organizational culture? How were student affairs staff and leaders affected as a result of budget cuts? In the context of budget reductions and strategies, what do SSAOs see as future financial issues in the profession? Participant responses revealed how SSAOs dealt with persistent budget reductions over an eight-year period, the impact of decisions, and ongoing challenges to their leadership. The results are reported in this chapter describing strategies the SSAOs used to reduce spending and increase income, the outcomes of budget cutting as perceived by the SSAOs, and the leadership qualities and skills they relied on when making these difficult decisions. Finally, the researchers developed critical lessons learned that may be considered as SSAOs and other student affairs staff are challenged in the coming years with what is anticipated to be lingering budget challenges.