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Grandparenting is a central family tie in later life, yet the mechanisms that sustain it shift as social, demographic, and cultural contexts evolve. This study examines how the mechanisms underlying grandparental caregiving in rural China have shifted over two decades (2001–2021), a period marked by mass labor migration, fertility decline, and the erosion of traditional patrilineal family norms. Drawing on eight waves of the Longitudinal Study of Older Adults in Anhui Province (N = 18,491 grandparent-adult child-wave observations), I use logistic regression with time-interaction terms to test four theoretically derived mechanisms: (1) cultural norms (patrilineal preference), (2) strategic investment (future-oriented reciprocity), (3) social exchange (present-oriented reciprocity), and (4) altruism (needs-based support). Results show that the son-linkage advantage in grandparental care declined significantly over time, reflecting a broader weakening of gender expectations in family support. Present-oriented social exchange strengthened as cultural mandates eroded, revealing a shift toward more negotiated and contingent forms of intergenerational assistance. Need-based altruism mechanism remained significant, but has adapted to the rise of migration-induced skipped-generation households. Strategic investment showed no significant change over time. Overall, these findings illuminate how demographic shifts—migration, smaller family size—and changing cultural norms jointly reshape the intergenerational family ties, with implications for both older adults’ well-being and child development in rapidly transforming rural societies.