Pre-service and in-service teachers nationwide are asking the following questions: Could we have been more prepared? COVID-19 has made public and transparent the digital inequalities of today’s schools, particularly for culturally and linguistically diverse (i.e., CLD) students and their families. How can technology be used in a proactive way regardless of context to identify and document both the technological needs and assets of students and their families beyond the question of who is or is not connected? This chapter encourages educators to shift their current technological pedagogical practices by exploring possible solutions that pull-in family biographies rather than follow prescribed virtual platforms and learning programs. Adopting a Freire-an perspective, this chapter posits that pre-service teachers as well as in-service teachers should view the use of technology as a tool that serves as the equalizer between home and school if used in ways that are agentive and transformational.