Background/Context: Digital life raises dilemmas that elude straightforward courses of action. These dilemmas are consequential to civic life, where participatory practices intersect with digital affordances to lend new power, stakes, and public consequences (Kahne et al., 2015). It is essential that students be able to recognize digital dilemmas and grapple with them in nuanced ways before acting (James, 2014). These realities engender calls for redesigning civic education for the digital age (Kahne et al., 2016). Engaging students with complex, authentic dilemmas builds on a rich tradition in moral education (Kohlberg, 1975). For educators on the front lines of this work, reflecting on polarizing digital civic dilemmas is an important precursor to effective classroom facilitation (Hess, 2005). Purpose and Research Questions: Doxing is the use of public social media to reveal personal information about an individual, often with the intent of inviting public shaming for their speech or other actions (Douglas, 2016). Doxing is a signature dilemma of today's age that surfaces fundamental questions about freedom, privacy, and accountability. The current study examines educators' varied responses to a doxing dilemma to illustrate how digital civic dilemmas can raise substantive themes for New Civics education. We ask: How do educators respond to a doxing dilemma? What considerations do they raise to justify different stances? Research Design: We draw on data from a larger survey about digital citizenship to examine views of educators (N = 769) who live and work with adolescents in varied contexts throughout the United States and in more than two dozen international contexts. We report on educators' responses to the doxing dilemma based on an inductive analysis of their open-ended responses. Findings: The focal dilemma is indeed polarizing: 47% (n = 361) of educators surveyed agreed with the doxing case, while 53% (n = 408) disagreed. Respondents' justifications reveal how the dilemma evokes reflection on the intersections of digital life with reasonable expectations of privacy, the bounds of constitutional rights and legal protections, salient moral principles, the importance of accountability and consequences for actions, and more. Conclusions/Recommendations: As educators are tasked with preparing youth for a New Civics era, we argue that digital civic dilemmas merit use in educator professional development settings and, ultimately, with students. Educators' perspectives on the doxing dilemma surface diverse considerations, which we reframe as ten questions to guide and deepen engagement.