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One Laptop per Child designed a laptop meant to transform educational practices across the Global South. Drawing on seven months of ethnographic fieldwork, this paper explores the lives of two “success stories”—those few exemplars for whom the laptop did seem to resonate. In OLPC’s eyes, these youths’ motivations were a matter of them finding something irresistible about engaging deeply and meaningfully with the laptop. But this paper uncovers a much more complicated story, rooted instead in connected learning and, ultimately, cruel optimism. In particular, even when the project’s promises appeared to be fulfilled, its individualist focus failed to shift the larger structural inequalities—gender, language, social class, and more—that marginalized these youth.