This study examines the perspectives and lived experiences of 10 urban secondary mathematics teachers from two epicenters of COVID-19 in the United States regarding their transition to digital learning during the 2019-2020 academic year. We use case study methodology with phenomenological interviews to gather insights into the teachers' efforts to modify their mathematics instruction and curriculum while navigating observed digital inequities and new digital tools for mathematics teaching. We also report on the teachers' targeted attempts to bridge home and school while problematizing the threatened humanistic aspect of remote teaching and learning. These frontline experiences recognize technology-associated systemic inequities in marginalized, urban communities and the need to strategize ways to implement equity-oriented technology integration that benefits all learners, especially urban youth. By critically examining digital education in the urban context, crucial conversations can transpire that critique (and disrupt) the digital divide in mathematics education and open doors for other stakeholders to broadly discuss the logistics and implications of digital education to enhance new ways of teaching and learning.