Wearable devices have become more common for the average consumer. As devices need to operate with low power, many devices use simplified security measures to secure the data during transmission. While Bluetooth, the primary method of communication, includes certain security measures as part of the format, they are insufficient to fully secure the connection and the data transmitted. Users must be made aware of the potential security threats to the information communicated by the wearable, as well as be empowered and engaged to protect it. In this paper, we propose a method of identifying insecure environments through crowdsourced data, allowing wearable consumers to deploy an application on their base system (e.g., a smart phone) that alerts when in the presence of a security threat. We examine two different machine learning methods for classifying the environment and interacting with the users, as well as evaluating the potential uses for both algorithms.