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This paper presents preliminary findings from an ongoing study of advocacy organizations pursuing reforms to transportation systems in several U.S. cities. For this paper, the findings and discussion center on the Atlanta, Georgia, region based upon thirty-four interviews with advocates conducted between 2015 and 2022. These interview data show that the racial dilemma, deciding between a “color-blind” or a “race-forward” advocacy strategy, represents a fundamental organizing issue for transportation advocates. In addition, these data support a conclusion that organizations with less access to power structures tend to engage in “race-forward” approaches, while those organizations with more access to power structures tend to employ “color-blind” approaches. The paper concludes that the racial dilemma, central in almost all issue areas in U.S. politics over the past several decades, is likely to continue as a fundamental challenge for advocates working on transportation justice and many other fields, including at state and local levels.