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The commercial sexual exploitation of children via the Internet (technology facilitated CSEC) is recognized as a serious crime; however, rates of prosecution are low. Given the egregious nature of technology facilitated CSEC and the complexity of these cases, it is important to understand and address the barriers state and federal prosecutors face when these cases go to trial. The current study qualitatively explored prosecutors’ perspectives on the barriers and frustrations they face prosecuting cases involving technology facilitated CSEC. Participants were 22 state and federal prosecutors who had an average of 9 years of experience working on cases involving technology facilitated CSEC. Each participated in a 30–45-minute interview via phone that was digitally recorded and transcribed verbatim. After being checked for accuracy, interviews were imported into a qualitative data analysis program and coded using a content analysis approach. Three distinct themes related to prosecutors’ experiences emerged from the data including: (1) Frustrations with awareness; (2) Inequitable resources; and (3) Inconsistent legal consequences. Findings highlight areas for training within the legal system, as well as loopholes that may inadvertently perpetuate inequities related to race, gender, and sex work. These findings, including their implications for future research and practice, will be discussed.