Technology and digital media are increasingly present in today’s classrooms, often used as tools for learning, connectivity, or even subversion. This dissertation project examines how everyday cybernetic practices–the blurring of the boundaries between human and machine, and between the physical and non-physical (Haraway, 2006)–are intentionally leveraged in the individual and collective development and enactment of expertise. Specifically, I explore how diverse undergraduate novice teachers, representing a range of majors, ethnicities, nationalities, and language practices, participated in a hybrid (online/in-person) education practicum course aimed at developing critical practices of service learning and engaged scholarship.This study is grounded in Cultural Historical Activity Theory (Engeström, 1999) which posits that learning is situated and dependent on social, historical, and cultural contexts that we navigate in our everyday. Following this theory, I examine how learning is mediated by material and psychological tools that are passed down through generations but always have the potential to be changed and transformed (Cole, 1996). Special attention is paid in this study to the way that digital tools, in the age of the cyborg (Haraway 2006; Lupton, 2012), can be transformed across timescales in ways that allow us to trace a person’s history of engagement with material and psychological tools almost instantly.As a social design-based experiment (Gutiérrez & Jurow, 2016), this research project employed ethnographic and social data analytic methods to illuminate cyclical and iterative processes of collaborative inquiry and co-operation (Goodwin, 2017) when students used custom-designed, state-of-the-art digital collaboration tools, across multiple sites (digital and face-to-face) of learning. To this end, data included video recordings of classroom interactions, field notes generated by study participants and myself, digital artifacts, back-end network analytics, student surveys and semi-structured interviews. By employing analytic tools from actor-network theory (Latour, 1996) as well as participation frameworks (Goodwin, 2007), this study aimed to illuminate (a) the discursive and textual features of face-to-face and online collaboration; (b) the tools and contexts that mediate these practices; and (c) the relationship between digital and face-to-face interactions and the development and sharing of expertise.Findings demonstrate that in tool-dense spaces learners engaged in robust collaborative inquiry that leveraged the connectivity and rhetorical affordances of digital technologies. The first iteration of the designed study, where the online aspect of the course was intentionally integrated into face-to-face interactions in our class, highlights how undergraduate novice teachers make use of their cyborg selves to openly share and develop expertise around teaching and learning. Over the course of this iteration, the following theories of collaboration and learning emerged: (1) Sustained attention to the social organization of learning in the design of a hybrid course resulted in collaboration at the intersection of the digital and in-person interactions that are characterized as meshworks marked by careful relationship building, and the creation, sharing, and remixing of syncretic (Gutiérrez, 2008) digital artifacts/texts across the digital and physical terrains; and (2) Through this collaborative meshwork of enactment of expertise, undergraduates begin to collectively develop models for teaching and learning. Further analysis of the composition and archiving practices that were fostered by the design of this course also illuminate the following: (1) When everyday practices of digital production and curation are privileged in a course, students engaged in archival processes by means of which students curated their own and their classmates’ language, images, responses, likes, and pins (cf. DeKoskink, 2016; Gutierrez, 2008) that then became salient compositional resources; (2) These multimodal, translingual, and “transmodal” (Lizárraga, Hull & Scott, 2015) archives then informed the writing of a variety academic texts; and (3) Syncretic texts that merged everyday and academic knowledge served as resources for the appropriation of socio-critical literacy perspectives. This research has implications for both the research and design of learning environments that aim to leverage digitally-mediated collaboration and multimodal composition. Methodologically, this study highlights the need for employing a variety of analytical tools from the digital humanities and sociocultural disciplines in order to understand the complex ways that undergraduates connect and collaborate at the intersection of the digital and face-to-face. The findings of this dissertation further highlight the necessity of designing courses at the undergraduate level that recognize the fluidity with which learners navigate virtual and in-person terrains in everyday activity of meaning-making and knowledge production, and nurturing of social relationships. This work also contributes to understandings of how undergraduate novice teachers develop notions of service learning and engaged scholarship in an increasingly digitized and interconnected world.