Among the flurry of executive orders signed by President Donald Trump in the early days of his second term were two orders signaling the administration’s intent to pressure private-sector organizations, including nonprofits, regarding their diversity, equity, and inclusion (“DEI”) practices. Nonprofits receiving federal funding face heightened compliance and financial risks, as do nonprofits that include racial preferences in their grant, scholarship, and fellowship programs and that provide preferences for those with protected characteristics in their employment policies and practices. Nonprofits can begin to assess legal and nonlegal risks by knowing their organization’s values and risk tolerance, examining its funding streams, scrutinizing DEI initiatives, and assessing culture.