Frequent renewal of digital devices accounts for a large share of their environmental impact because of fabrication environmental costs. This renewal is often attributed to sociocultural phenomena (e.g. presentation of self or persuasive marketing) and to broken hardware (e.g. shattered screens or degraded batteries). We investigate a complementary aspect: how people live with devices as they are gradually becoming obsolete. We present a qualitative interview-based study with 18 participants on the role of software factors on the feeling of smartphone obsolescence. We identify three types of factors pushing for device renewal: upgrade issues, storage issues, and malfunctions. We find that these issues accumulate over time until a threshold is passed leading to renewal: we define this process as an obsolescence path. This threshold is often tied to contextual and social concerns. We also outline the various strategies people use to prolong the life of the almost obsolete devices. Our results show that hardware and software obsolescence are tied, and should be considered together as they trace obsolescence paths. Based on these observations, we identify design opportunities to extend the lifespan of devices.