Android's fragmented ecosystem makes the delivery of security updates and OS upgrades cumbersome and complex. While Google initiated various projects such as Android One, Project Treble, and Project Mainline to address this problem, and other involved entities (e.g., chipset vendors, manufacturers, carriers) continuously strive to improve their processes, it is still unclear how effective these efforts are on the delivery of updates to supported end-user devices. In this paper, we perform an extensive quantitative study (Aug. 2015 to Dec. 2019) to measure the Android security updates and OS upgrades rollout process. Our study leverages multiple data sources: the Android Open Source Project (AOSP), device manufacturers, and the top four U.S. carriers (AT&T, Verizon, T-Mobile, and Sprint). Furthermore, we analyze an end-user dataset captured in 2019 (152M anonymized HTTP requests associated with 9.1M unique user identifiers) from a U.S.-based social network. Our findings include unique measurements that, due to the fragmented and inconsistent ecosystem, were previously challenging to perform. For example, manufacturers and carriers introduce a median latency of 24 days before rolling out security updates, with an additional median delay of 11 days before end devices update. We show that these values alter per carrier-manufacturer relationship, yet do not alter greatly based on a model's age. Our results also delve into the effectiveness of current Android projects. For instance, security updates for Treble devices are available on average 7 days faster than for non-Treble devices. While this constitutes an improvement, the security update delay for Treble devices still averages 19 days.