Over the past decade, mobile devices such as smartphones have become increasingly common as a form of handheld computing platform. The use of mobile applications on these mobile devices is experiencing unprecedented rates of growth. However, when using mobile applications, users are often requested to give context information. Such requests have led to growing privacy concerns. This paper proposes the use of context-awareness to improve single sign-on (SSO) solutions so that mobile users can protect their private information. A privacy-based adaptive SSO (ASSO) may be able to increase users’ perceived ease of use of the system and give service providers the necessary authentication security for their applications. The study was based on data gathered from 168 participants as part of the Lausanne Data Collection Campaign. This was led by the Nokia research center in Switzerland and used Nokia N95 phones. The analysis of SVM showed our expectations to be correct. Consequently, a new business model for mobile platforms has been proposed to reinforce our claim that privacy-friendly value propositions are possible and can be used to obtain a competitive advantage.