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Twenty-first century technology has rapidly changed the ways in which people interact, connect, and network utilizing smart devices as part of our everyday existence. This transformation is also part of the changing landscape of qualitative fieldwork. While traditional modes of data collection are still important to ethnography, interview, and focus group methodologies, a burgeoning set of new instruments are being infused in this work. This presentation examines the shift in qualitative data collection on carceral spaces. Exploring two studies, this paper highlights how technology has changed data collection dynamics. In the first study, I discuss my fieldwork within a community-based reentry organization as well as the surrounding neighborhood and how because these spaces are highly policed and monitored, carceral logics can create suspicion amongst residents of outsiders. The second study highlights the convenience and ability to transcend borders and time zones to discuss, engage, and conduct research over space and time.