According to the U.S. Department of Education's National Center for Education Statistics, in the fall of 2020, 72.8% of U.S. postsecondary students were enrolled in distance education courses--up from 36.3% in the fall of 2019. While this surge may be explained by a number of factors, one of the most significant factors is the COVID-19-induced pivot to online learning. The rapid and intense expansion in distance education due to COVID-19 offered learners some sense of continuity in their studies, but it also revealed stark inequities in learner resources and access--especially for students of Color and students from lower-income households. Further, as COVID-19 spread, the U.S. roiled in a "twin pandemic" of racial injustice that continued to metastasize--spawning more pain-points such as online environments where racism became unmasked when face-to-face norms were abandoned. These revelations about the shadow side of online learning are particularly concerning in the context of leadership education and its commitment to inclusion, collaboration, and holism. Given this new context for online leadership education, the purpose of this piece is to reflect on how the Journal of Leadership Education has shepherded the journey of online leadership education and what the future of this journey might look like for online leadership educators committed to change. Scaffolded by the Community of Inquiry model, we offer promising practices that address cognitive, social, teaching, and learner presence in the pursuit of culturally relevant/sustaining and equitable online leadership education.