Signs of a leadership crisis in community colleges have been building over the past decade, with one study predicting that as many as 84 percent of current presidents could retire within the next 10 years. Several plans of action are under way to handle this changing of the guard, including more leadership-preparation programs offered by such groups as the American Association of Community Colleges, the American Council on Education, and the League for Innovation in the Community College, to name a few. What is missing in this whirlwind of activity, however, is an acknowledgment of the critical issues that rural community colleges and their leaders face. Rural community colleges in fact comprise 60 percent of all community colleges, making them too numerous to ignore. Under the worst-case scenario, more than 1,000 presidential searches could take place in the next decade to fill vacancies in rural locales. Isolated locations, lower pay, and a lack of cultural events all make it difficult to attract and retain rural college leaders. All these challenges require intentional planning for the pending leadership transitions in the heartland. This article offers several suggestions on how institutions, current leaders and mentors, and individuals can prepare.