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Through interviews with experienced moderators from PWUD forums on Reddit, we examine the unique nature of this work and its implications for HCI and content moderation research. We demonstrate that this work constitutes a distinct form of public health intervention characterised by three challenges: (1) high-stakes risk evaluation requiring pharmacological expertise, (2) time-critical crisis intervention spanning platform content and external drug market surveillance, and (3) navigation of structural conflicts where platform policies designed to minimise legal liability directly oppose community harm reduction goals. Our findings extend existing HCI moderation frameworks by revealing how legal liability structures can systematically undermine expert moderators' protective work, with implications for other marginalised communities facing similar regulatory tensions, including abortion care and sex work contexts. We identify two necessary shifts in sociotechnical design: moving from binary classification to multi-dimensional approaches that externalise competing factors moderators must balance, and shifting from low-level rule programming to high-level example-based instruction. However, we surface unresolved tensions around volunteer labour sustainability and risks of incorporating automated systems in high-stakes health contexts, identifying open questions requiring HCI research attention. 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