This dissertation investigates the pathways and causes of the development of glide deletion in Seoul Korean. Seoul provides fertile ground for studies of linguistic innovation in an urban setting since it has seen rapid historical, social and demographic changes in the twentieth century. The phenomenon under investigation is the variable deletion of the labiovelar glide /w/ found to be on the rise in Seoul Korean (Silva, 1991; Kang, 1997). I present two studies addressing variation and change at two different levels: a corpus study tracking the development of /w/-deletion at the phonological level and an articulatory study examining the phonetic aspect of this change. The corpus data are drawn from the sociolinguistic interviews with 48 native Seoul Koreans between 2015 and 2017. A trend comparison with the data from an earlier study of /w/- deletion (Kang, 1997) reveals that /w/-deletion in postconsonantal position has begun to retreat, while non-postconsonantal /w/-deletion has been rising vigorously. More importantly, the effect of preceding segment that used to be the strongest constraint on /w/-deletion has weakened over time. I conclude that /w/-deletion in Seoul Korean is being reanalyzed with the structural details being diluted over time. I analyze this weakening of the original pattern as the result of linguistic diffusion induced by a great influx of migrants into Seoul after the Korean War (1950-1953). In an articulatory study, ultrasound data of tongue movements and video data of lip rounding for the production of /w/ for three native Seoul Koreans in their 20s, 30s and 50s were analyzed using Optical Flow Analysis. I find that /w/ in Seoul Korean is subject to both gradient reduction and categorical deletion and that younger speakers exhibit a significantly larger articulatory gestures for /w/ after a bilabial than older generation, which is consistent with the pattern of phonological change found in the corpus study. This dissertation demonstrates the importance of using both corpus and articulatory data in the investigation of a change, finding the coexistence of gradient and categorical effects in segmental deletion processes. Finally, it advances our understanding of the outcome of migration-induced dialect contact in contemporary urban settings.