In February of 2011, Nokia cancelled all of its Linux-based phone projects in favor Windows Mobile. As a result, many of the engineers working on its Maemo-based phones left and founded Jolla. Given funding but no intellectual property, they created the new Jolla Phone and Sailfish OS, a combination of open source and proprietary components. The phones, now available in Nordic countries, also feature "smart covers" called "The Other Half", capable of anything from changing your theme to adding a keyboard to the phone. They also feature a full, open Linux environment, an Android compatibility layer, and many other appealing features. When we obtained these phones, we were immediately curious to explore them, and try to break things along the way. In this talk, we will explore the architecture of the phone and see where the weak points might be. Starting in the beginning, we will look into the phone's recovery, explain its layout and understand what security implications are present. We're also going to look at our process for looking for vulnerabilities in the stock operating system and the applications themselves. Public vulnerabilities will be discussed to understand what led to them and how they were patched. Exploitation of vulnerabilities in the context of the Jolla will also be covered, to help understand what protections or roadblocks the phone presents. Our exploration of "The Other Half" covers will also be discussed. We'll describe how they're architected, what we learned from interacting with the NFC and I2C interfaces, and any weak points that were discovered. A custom cover will be used to explore the possibility of malicious covers. Lastly, we will look at the application infrastructure and understand what it would take to test an application written for the Jolla environment. In the end, we will have covered broad topics in hardware and software, applicable to devices far beyond the one we cover in this talk.