With the development of increasingly advanced technologies, interactions with and via these technologies have become even more central to human activity. Technology is utilized in both sanctioned and unsanctioned ways within language and literacy classrooms around the world making questions, concerns, and curiosities around educational potentials and ethical consequences abundant (Holmes et. al, 2021). Even as online interactions across national, cultural, ideological, linguistic, and virtual borders become more frequent and complex, equity in these interactions has not increased and representation remains disproportionate (Acey et al., 2021). Material modes and tools of communicative practices are complicit in the ways groups and individuals engage amongst, and make meaning of, themselves and global peers. In this dissertation, I engage a New Materialist framework (Braidotti 2013; Barad 2007) to complicate notions of agency and authorship in my analysis of data from an ethnographically informed study exploring the meaning making and literacy practices of youth engaging in transnational, digital communication. This thesis examines the everyday digital literacy practices and material entanglements within which youth participants in Mexico, Uganda, and the United States make sense of themselves and others through materially-discursive practices (Barad 2007). Through my analysis, I found that in these engagements meaning making was an emergence of layered, local histories, and embodied experience. I also examined the differential roles similar technologies and platforms took up in different contexts finding that digital literacy holds the potential for both oppression and liberation. I end this dissertation with implications for research and pedagogy along with a call for researchers and educators to critically examine and responsibly engage with the unintended outcomes of digital literacy entanglements in order to inform critical language and literacy pedagogy that is relevant and responsive to the globalizing and digitally mediated landscape of the 21st century. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]