The aim of this study was to investigate caregivers’ experiences of complementary feeding (CF) among the Native Hawaiian and Other Pacific Islander (NHPI), and Filipino populations. Research focused on the timing of CF commencement, and the influence of transgenerational experience on feeding practices. The experiences and practices of those who fed human milk exclusively (HME), were compared to those who included infant formula (F&HM). Caregivers of a subset of 32 infants who were participating in a larger longitudinal study relating to CF and diet diversity, took part in voluntary in-depth interviews relating to CF practices. Interviews were recorded and transcribed. Two researchers analyzed interview transcripts. Interrater reliability and saturation were established. Institutional Review Board exemption was confirmed prior to study commencement. Interviews with 29 caregivers of infants were included in this study. Only infants of the F&HM group had an early introduction to complementary foods (<4 months of age). Caregivers reported receiving conflicting advice from healthcare professionals (HCPs) in relation to timing of the introduction of complementary foods. Nonetheless, the majority of caregivers reported following the advice of HCPs. Extended family (including grandparents) played less of a role in infant feeding, compared to previous generations. While transgenerational practices were valued and included, ultimately, the perceived health and safety of the practice for infants influenced decisions.