This article compares case studies to better understand how third grade teachers, serving low-income (including Title I) schools, adapted their instruction in the midst of a global pandemic to better support their students’ learning about locally-relevant civic issues. Civic perspective-taking components were embedded in the unit design with the aim of building deliberative, inclusive classrooms. The team designed lessons drawing from theories of culturally sustaining pedagogy. Using semi-structured interview data, we examined teachers’ reported thinking and perceptions about students’ needs and their own struggles to deliver purposeful, equitable instruction. Findings indicate that as teachers collaboratively designed the lessons they discussed how to balance relevance and sensitivity in relation to content that mirrored students lived realities. This study advances our understanding of what challenges teachers overcome to integrate culturally-sustaining practices in their social studies instruction.