The Obama administration has some improbable critics: members of the Historically Black College and University (HBCU) community. What started out as carefully worded commentaries have given way to more direct criticisms and complaints about the administration's policies affecting HBCUs. Although some of these gripes can be attributed to unfulfilled expectations of reciprocity after HBCUs supported Obama in both presidential elections, Marybeth Gasman and Heather Collins' assessment reveals a much more nuanced situation. Although the Obama administration has done more for HBCUs than many acknowledge, it has stumbled in some key policy areas. The White House's biggest failure, though, has been one of communication. HBCUs are themselves partly to blame for not presenting a united front when dealing with the administration. In this regard, they should take a cue from other Minority-Serving Institutions (MSIs), such as those educating Hispanic and Asian American & Pacific Islander students. To get at the heart of the HBCU criticism of the Obama administration, the authors reviewed open letters to the President and Secretary of Education, meeting minutes, federal budget allocations, interviews, and news articles over the last six years. The major concerns of HBCU leadership and advocates are summarized in this article and fall into three areas: finances, the proposed college ranking system, and personnel policies.