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There is growing recognition among researchers of the vital importance of criminal offenders’ perspectives in understanding, and thus better preventing, crime. To that end, qualitative methods, particularly in-depth interviews, are essential in developing nuanced and more accurate understandings of offenders’ lived experiences and criminal behavior. However, numerous practical and ethical challenges arise when trying to conduct interviews with criminal offenders, including access to participants, trust, and legal vulnerability. Drawing on experiences conducting qualitative in-depth interviews with criminal offenders across multiple carceral settings in two states, as well as with gang-involved participants from a high gun-violence community in Southern California, we discuss the challenges and opportunities encountered when conducting in-depth qualitative research in highly controlled and traditionally inaccessible spaces. For example, we address how institutional context creates pressures for both the researcher and participant, and how we attempted to navigate such issues during the data collection process. Directions for future research with criminal offenders in both carceral and non-carceral settings are also discussed.