This paper situates itself amid the debates on the “morality of proximity” and what it means in an era where the advancements of communication technologies are purported to have enabled time-space compression. Exploring the case of Filipino transnational families, where one or both parents have migrated for work, we train our lenses on how proximate and long-distance parenting is mediated, negotiated, and contested through the affordances of polymedia. In this paper, we seek to examine how polymedia is implicated in the transformation or reification of these care relationships and uncover the normative and gendered familial values at work. Despite a growing literature on transnational relationships and communication technologies, most studies have focused mainly on communication from migrants to the homeland (and vice-versa), portraying a more bilateral direction of care and communication. Thus, the more complex and circuitous dynamics of transnational familyhood are elided. Transnational parenting also involves multilateral negotiations of competing interests, aspirations, and subjectivities of people “left-behind”. By focusing on the findings from a qualitative and longitudinal study of left behind carers (n=28) and children (n=28), we explore how the discourses and practices of transnational parenting are negotiated and contested, as “proxy” but proximate care in the homeland intersects with the long-distance care from migrant parents mediated through various ICTs. By venturing into how the “left-behind” members of transnational households (re)negotiate their care relationships and subjectivities through various communication technologies, we hope to complicate binary understandings of mobilities and immobilities, proximate and distantiated care, and “real” and “virtual” spatiotemporalities.