This article analyzes the influence of ICTs use on transnational connections and on their perpetuation over time within multigenerational kinship groups dispersed in several countries. Evidence from a multi-sited ethnographic research dedicated to migration from the Azores archipelago (Portugal) to the province of Quebec (Canada) provides information about factors explaining transnational practice over several decades. Our data indicate an overall intensification of transnational contacts due to increasing accessibility of new technologies. However, this process takes place in a family environment characterized by multi-connectedness, a capacity to maintain multiple active ties with siblings living in various countries and using multiple modalities. Transnational practices are transformed, incorporating ICTs in new routines of communication that complement already existent ones. We consider that this process sustains the ongoing transformation of family networks by younger generations’ active participation in transnational connections, but pre-existing relations are fundamental to transnational connections.