Wearable devices are becoming increasingly important, helping us stay healthy and connected. There are a variety of app-based wearable platforms that can be used to manage these devices. The apps on wearable devices often work with a companion app on users’ smartphones. The wearable device and the smartphone typically use two separate permission models that work synchronously to protect sensitive data. However, this design creates an opaque view of the management of permission-protected data, resulting in over-privileged data access without the user’s explicit consent. In this paper, we performed the first systematic analysis of the interaction between the Android and Wear OS permission models. Our analysis is two-fold. First, through taint analysis, we showed that cross-device flows of permission-protected data happen in the wild, demonstrating that 28 apps (out of the 150 we studied) on Google Play have sensitive data flows between the wearable app and its companion app. We found that these data flows occur without the users’ explicit consent, introducing the risk of violating user expectations. Second, we conducted an in-lab user study to assess users’ understanding of permissions when subject to cross-device communication (n = 63). We found that 66.7% of the users are unaware of the possibility of cross-device sensitive data flows, which impairs their understanding of permissions in the context of wearable devices and puts their sensitive data at risk. We also showed that users are vulnerable to a new class of attacks that we call cross-device permission phishing attacks on wearable devices. Lastly, we performed a preliminary study on other watch platforms (i.e., Apple’s watchOS, Fitbit, Garmin OS) and found that all these platforms suffer from similar privacy issues. As countermeasures for the potential privacy violations in cross-device apps, we suggest improvements in the system prompts and the permission model to enable users to make better-informed decisions, as well as on app markets to identify malicious cross-device data flows.