Social sustainability is becoming an increasingly important topic in design practice, calling for more contextual perspectives on the process of design for social sustainability. This paper presents a retrospective case study analyzing the design process of a serious game which aimed to empower teenagers to organize events to strengthen community bonds. The community context in which the collaborative project took place underwent significant contextual changes due to the COVID-19 pandemic. Analysis using the Ecologies of Contestation framework shows the influence of multiple contextual levels (Socio-cultural, Power, Constructed, and Values-based) on the design process. Moreover, the paper discusses multiple contextual factors which influenced the design process and presents four suggestions for designers to anticipate and benefit from dynamics in these contextual elements. The suggestions regard (1) integrating the temporal dimension in the collaborative design processes, (2) carefully considering (value) alignment between actors, (3) leveraging values in the collaborative design process, and (4) acknowledging and responding to the multilayered nature of communities throughout the design process. As such, this paper explores the relationships between the community context and the collaborative design process to contribute to more resilient design practices.