This article addresses the limited understanding of how variegated practices of everyday automobility shape – and are shaped by – ageing processes of older adults in urban contexts, focusing on Brescia, Northern Italy. While automobility, driving and driving cessation are often studied as functional aspects of older adults’ (im)mobility, their relational dimensions – spanning multiple and diverse practices – remain largely under-explored. The research examines how older adults navigate the contradictions and challenges of urban life, health conditions and social structures through relational automobilities. Drawing on an ongoing ethnographic study, the article highlights how automobility serves simultaneously as a resource, a limitation and a medium for forging and sustaining social, emotional, geographical and material relationships. The findings reveal that diverse practices and experiences of automobility are deeply embedded in affective economies, interdependencies and the biopolitics of ageing, shaping – and being shaped by – the lived experiences of older adults. By conceptualizing automobility as a socio-material and relational process, the article aims at bridging critical gerontology and mobilities studies, offering new insights into how ageing and mobility practices co-produce ageing selves and conditions of being (im)mobile. This study contributes to ongoing debates in critical gerontology by problematizing dichotomic understandings of older adults’ experiences in terms such as independence versus dependence and mobility versus stasis, while also informing urban policies aimed at fostering inclusive mobility practices. This article emphasizes the need to address the socio-material and relational networks underpinning automobility, offering a nuanced perspective on the interplay between mobility, ageing and urban life.