In our work—Michelle as a technology integration specialist at a suburban high school in Massachusetts, and Spencer at a community college library in Illinois—we have seen the digital divide impact students, faculty, and staff in intersecting and distinct ways. We understand that the digital divide in our communities stems from and reinforces entrenched inequities, and so it is of paramount importance that we work to bridge these gaps. Our backgrounds in critical media, information, and digital literacies also alert us to the ways in which “bridging the digital divide” can lead to practices that may be coercive, overly expose users to surveillance technologies, and result in information overload for students and employees. As we reflect on evolving understandings of the digital divide and the complexities uncovered when working to bridge these gaps, we acknowledge our own privileges and opportunities to learn more about this vast and important topic.