Chromecast is a small HDMI device that provides users with an easy way to stream online videos and music to the TV. The Chromecast out-of-box experience (OOBE) has been lauded by reviewers and consumers for its simplicity and ease of use. Even though setting up Chromecast is pretty simple, we found that without proper guidance there were several ways that users could fail. This case study will present the different challenges the team faced in designing the Chromecast OOBE and the different options the team explored. We will also describe our user research process and how the user experience team worked with engineers and product managers to implement a simple and easy OOBE.