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Gifts have been well studied in a variety of contexts. This holds true for those participating in healthcare. Yet much of this existing literature misses analysis of gifting practices to ill folk. Utilizing in-depth interviews with 50 millennial cis-gendered females diagnosed with hormone-positive cancers and content analysis of online gift guides, this article provides a glimpse into this specific social exchange from the perspective of ill individuals. Findings show that in this high-stakes environment, both positive and negative subjective interpretations arise from gifting that are deeply connected to the circumstances of serious illness and mortality. To maximize the likelihood of positive gifting, some individuals defy norms and proactively curate gifts to suit their desires through explicit demands and proxies, thereby cultivating giftee self-determination. Engaging in such actions increases a sense of personal control and autonomy in a situation that feels helpless. Also discussed are the possible impacts of gifting guides.