Quick Access is a machine-learned system in Google Drive that predicts which files a user wants to open. Adding Quick Access recommendations to the Drive homepage cut the amount of time that users spend locating their files in half. Aggregated over the ~1 billion users of Drive, the time saved up adds up to ~1000 work weeks every day. In this paper, we discuss both the challenges of iteratively improving the quality of a personal recommendation system as well as the variety of approaches that we took in order to improve this feature. We explored different deep network architectures, novel modeling techniques, additional data sources, and the effects of latency and biases in the UX. We share both pitfalls as well as successes in our attempts to improve this product, and also discuss how we scaled and managed the complexity of the system. We believe that these insights will be especially useful to those who are working with private corpora as well as those who are building a large-scale production recommendation system.