When talking with New York City educators about the circumstances of teaching during the upheavals wrought by COVID-19, common terms get repeated: "brutal," "chaotic," "confusing," "traumatic," "disorienting," "sad," and "lonely." While art education often includes digital tools and platforms, and many educators explore and produce digital media to engage student learners, the new realities of remote teaching left many teachers outside of familiar teaching methods and comfort zones. On top of the immediate concerns and questions about how to reach students and shift learning online, the pandemic exposed stark inequalities across race, class, and gender demographics that have always plagued education. This instructional resource article is written as a conversation between two teachers and an academic colleague who realized a shared commitment to fostering community and student collaboration through digital media at the height of the 2020-2021 pandemic. Written as an interview/dialogue, the three educators initially met in the graduate program in Art + Education at New York University (NYU) and have continued to stay in touch to share practices, challenges, and friendship. Caitlin Gibbons teaches media and filmmaking at Digital Art & Cinema Technology High School, a public high school serving predominantly Black and Latinx students (49% and 37%, respectively), with 81% of students eligible for free or reduced lunch, in Brooklyn, New York. Alexis Lambrou teaches photography and media literacy at Bard High School Early College Manhattan (BHSEC), which has a student population that includes 27% Asian, 13% Black, 20% Latinx, and 38% White, with 41% of students eligible for free or reduced lunch. Jessica Hamlin is a clinical faculty member of the Art + Education program at NYU, which has a focus on contemporary art, social justice education, and critical multiculturalism. During a conversation among NYU Art + Education alumni, Jessica suggested to Caitlin and Alexis that they share their experiences of teaching during the pandemic because each were facilitating experiences with digital media that prioritized student voice, opportunities to visualize their unique realities, and connect with others who were experiencing related yet distinct pandemic realities. Both educators were enacting forms of collaboration that "create a culture of caring" that felt timely and important to share with other educators.