In the past 7 years of working at and in community colleges, the author has seen two distinct trends: (1) Community colleges appear to be ushering in a new era of advancement; and (2) Community colleges themselves are often the biggest impediment to successful advancement efforts. Despite millions of grateful learners and business and community leaders who see the positive economic and social impact of community colleges, those at the institutions too often relegate themselves to second-class status. However, community colleges are increasingly completing successful major campaigns. More than half of the community colleges responding to a recent Council for Advancement and Support of Education (CASE) survey said they are planning, conducting, or completing a major fundraising campaign. This article discusses what successful community colleges have in common when it comes to fundraising and what successful alumni programs do to raise money for community colleges.