Wearable computing is gaining more and more interest as new “wearables,” intended for both work and leisure, are introduced. This trend brings benefits and challenges; for instance, the potential to improve work processes and issues related to IT management and privacy. The introduction and use of wearable computing provides opportunities to improve and reengineer work processes in organizations but can at the same time introduce alignment problems, as users in organizations may adopt the new technology before organizations are prepared. Further, alignment problems posed by the emerging trend, “Bring Your Own Device” (BYOD), are discussed. In addition, as in the cloud computing area, needed and necessary supportive legal frameworks have not yet fully addressed the new wearable computing technology. In the light of recent developments regarding global intelligence gathering, security and privacy concerns must be given careful consideration. Different alignment concepts for managing security challenges and legal aspects related to wearable computing, such as cultivation, care, hospitality, and care with hospitality, are discussed in the chapter.