Since the beginning of our journey, we have tried to create a wearable experience starting from our existing handheld app. A first working solution has been achieved just taking advantage of the WearableExtender that has allowed us to easily extend the status bar notifications, providing detailed info and extended functionalities to the wearable device. Even if this approach can work for the majority of the applications and it is really straightforward to achieve, it has some drawbacks in terms of achievable features and availability of content on the smartwatch. In fact, if the smartphone and the wearable device are not coupled, the latter one cannot offer any more access to the previously shown content. Keeping in mind that the wearable device is not a substitute of the handheld one but more like an extension that should try to simplify the user life, we have then exposed a limited number of functionalities into a custom wearable app. In order to achieve this result both applications currently share a common module but are decoupled in terms of single application modules. In this way it is possible to recycle and share code elements like the ContentProvider, the models and common utilities but at the same time keep distinct the different platform based implementations. In ‘Pimp my Wear’, this solution has led us to a wearable application that can be used by the user even if the two devices are temporarily disconnected but at the same time to a situation where the content gets out-synced. In this chapter we are going to have a look at how the Wearable Api can help us exchanging and syncing data between the two different devices.