Background or Context: This research is situated against the backdrop of viral racial violence, global uprisings for racial justice, a polarizing presidential election, the insurrection at the U.S. Capitol, widespread economic precarity, and the COVID-19 pandemic. Alongside such urgent reminders of the need for liberatory education, the daily routines of educators were upended in response to an unprecedented, emergency shift to remote schooling. As such, this study was designed to listen and learn from teachers about their experiences during a historic time. Purpose, Objective, Research Question, or Focus of Study: Digital pedagogies are often conceptualized and enacted as separate from race-conscious, culturally responsive approaches to teaching and learning. However, the transformative time in which this research took place underscored the importance of weaving these pedagogical approaches together. As such, this study was guided by the following questions: (1) How did the sociopolitical context of teaching and learning during the pandemic impact teachers’ approaches to and development of culturally responsive digital pedagogies? (2) What obstacles and/or successes did teachers encounter as they transitioned to remote teaching while trying to enact culturally responsive pedagogies? Research Design: We designed this research using a critical, collaborative, and humanizing methodological approach that began with a national survey of K–12 teachers located across the United States ( n = 126). Results from the survey were then used to recruit participants and to contextualize and inform semi-structured follow-up interviews ( n = 58). With the intention of listening and learning from teachers, we also took a constructivist grounded theory approach that allowed us to develop findings that remained grounded in what participating teachers considered most important about their experiences during this time. Findings: Our data illuminates how multiple, compounding crises made their way into the classroom in ways that contoured and constrained what was possible for teachers’ culturally responsive digital pedagogies. As macro-level events prompted teachers to focus on developing their own racial literacy and prioritizing the health and well-being of their students over academic learning, responses from school and district leadership at the meso/exo-level kept them gravitating toward the technology and pedagogies that felt most familiar. At the micro-level, the virtual nature of teaching and learning blurred everyday boundaries between home and school, causing teachers to develop a greater sense of empathy for the students and families they were serving, while simultaneously experiencing increased surveillance and fears of pushback about topics that could be deemed political. As these contexts converged, we identified how participants chose to prioritize some aspects of culturally responsive teaching over others, while also responding to the tense political landscape and fears of virtual surveillance in agentic, contextual, and idiosyncratic ways. Conclusions or Recommendations: This research highlights the many layers of complexity and context that shape teachers’ pedagogical decision making, especially during times of crisis, polarization, and upheaval. Although policymakers often pay attention to the meso/exo- and micro-level contexts of teaching and learning, the role of the broader sociopolitical, racial, and economic context is too often overlooked. Therefore, we argue that if we want to improve teaching and learning, we need to invest in structural changes that will improve the lives of students and teachers both inside and outside of school. In addition to underscoring the importance of attending to the full ecology of inequality, our findings also highlight the necessity of shifting toward research, policies, and practices that consider how humanizing, culturally responsive, liberatory, and digital pedagogies can work in tandem with one another to better meet the needs of students in our increasingly unequal and technologically advanced society.