In the context of accelerated digitalization, this chapter proposes a cultural and systemic perspective on contemporary technological ecosystems. It addresses three key dimensions through an interdisciplinary lens: (1) the conceptual evolution of the product, which has shifted from static object to node in dynamic sociotechnical networks; (2) the transformation of the user into an interconnected subject engaged in multi-actor interactions via intelligent systems; and (3) the emergence of digital ecosystems as living cultural environments, whose sustainability depends on symbolic resonance, user agency, and contextual adaptability. The study suggests the potential of technological ecosystems to influence meanings, norms, and forms of social coexistence. It analyzes the cultural impacts of such ecosystems at the individual, collective, and heritage levels, from emotional bonds and identities to symbolic cohesion and memory preservation. Likewise, it highlights the role of culture not only as a product of these systems but also as a filter shaping acceptance and use. Finally, the text outlines some key challenges for the cultural sustainability of digital ecosystems, such as cultural homogenization, sociotechnical exclusion, and the redistribution of agency in automated contexts. It then introduces several emerging methodologies for designing such systems, to illustrate how certain approaches address these challenges. The findings suggest the value of considering situated, relational, and sustainable approaches, understanding the design of technological ecosystems as an opportunity to contribute to the configuration of cultural environments and the design of futures.