This paper offers an analysis of Middle Eastern American civil rights organizations’ efforts to confront racist Islamophobia over the past decade and a half based upon qualitative research including interviews and content analysis. It describes the strategic “racial dilemma” posed by the racial politics that have dominated US elections and policymaking throughout this period. This racial dilemma comes about due to the lack of mainstream acceptance of Islamophobia as a reprehensible form of racism, meaning that civil rights advocates cannot easily make claims that discriminatory policies and programs are morally wrong as well as ineffective. As a result, even amid the rapid expansion of policies and practices that systematically discriminated against Middle Eastern Americans, civil rights advocates struggled to find a foothold in political or policy circles. Tracing the similarities and differences between advocacy efforts in three periods—the Bush, Obama, and early Trump eras—shows that this racial dilemma has precluded several strategic options for advocates as they tried to expand civil rights protections for Middle Eastern Americans. Civil rights advocacy in the Bush era largely conformed to “color-blind” ideology, with advocates turning to religious freedom and other frames instead of racism to argue against discriminatory policies, and this enabled some victories. For much of the Obama era, this “color-blind” approach remained dominant, but some race-conscious advocacy began to emerge in its later years. Finally, the Trump era threatens to close off some of the avenues that had been available for advocates in the Bush and Obama eras. State agencies may reconfigure or cancel their so-called outreach and civil rights enforcement efforts, while extending their so-called counterterrorism and national security efforts. This may necessitate significant strategic shifts among Middle Eastern American advocates in the years ahead. The paper concludes with a brief discussion of potential strategic solutions to the racial dilemma presented during and after the expansion of Islamophobic racism seen in 2016 US elections.