People engage with multiple online services and carry out a range of different digital transactions with these services. Registering an account, sharing content in social networks, or requesting products or services online are a few examples of such digital transactions. With every transaction, people take decisions and make disclosures of personal data. Despite the possible benefits of collecting data about a person or a group of people, massive collection and aggregation of personal data carries a series of privacy and security implications which can ultimately result in a threat to people's dignity, their finances, and many other aspects of their lives. For this reason, privacy and transparency enhancing technologies are being developed to help people protect their privacy and personal data online. However, some of these technologies are usually hard to understand, difficult to use, and get in the way of people's momentary goals. The objective of this thesis is to explore, and iteratively improve, the usability and user experience provided by novel privacy and transparency technologies. To this end, it compiles a series of case studies that address identified issues of usable privacy and transparency at four stages of a digital transaction, namely the information, agreement, fulfilment and after-sales stages. These studies contribute with a better understanding of the human-factors and design requirements that are necessary for creating user-friendly tools that can help people to protect their privacy and to control their personal information on the Internet. / People engage with multiple online services and carry out a range of different digital transactions with these services. Registering an account, sharing content in social networks, or requesting products or services online are a few examples of such digital transactions. With every transaction, people take decisions and make disclosures of personal data. Despite the possible benefits of collecting data about a person or a group of people, massive collection and aggregation of personal data carries a series of privacy and security implications which can ultimately result in a threat to people's dignity, their finances, and many other aspects of their lives. For this reason, privacy and transparency enhancing technologies are being developed to help people protect their privacy and personal data online. However, some of these technologies are usually hard to understand, difficult to use, and get in the way of people's momentary goals. The objective of this thesis is to explore, and iteratively improve, the usability and user experience provided by novel privacy and transparency technologies. To this end, it compiles a series of case studies that address identified issues of usable privacy and transparency at four stages of a digital transaction, namely the information, agreement, fulfilment and after-sales stages. These studies contribute with a better understanding of the human-factors and design requirements that are necessary for creating user-friendly tools that can help people to protect their privacy and to control their personal information on the Internet.

The amount of personal identifiable information that people distribute over different online services has grown rapidly and considerably over the last decades. This has led to increased probabilities for identity theft, profiling and linkability attacks, which can in turn not only result in a threat to people’s personal dignity, finances, and many other aspects of their lives, but also to societies in general. Methods and tools for securing people’s online activities and protecting their privacy on the Internet, so called Privacy Enhancing Technologies (PETs), are being designed and developed. However, these technologies are often seen by ordinary users as complicated and disruptive of their primary tasks.   In this licentiate thesis, I investigate the usability aspects of three main privacy and security enhancing mechanisms. These mechanisms have the goal of helping and encouraging users to protect their privacy on the Internet as they engage in some of the steps necessary to complete a digital transaction. The three mechanisms, which have been investigated within the scope of different research projects, comprise of (1) graphical visualizations of service providers’ privacy policies and user-friendly management and matching of users’ privacy preferences “on the fly”, (2) methods for helping users create appropriate mental models of the data minimization property of anonymous credentials, and (3) employing touch-screen biometrics as a method to authenticate users into mobile devices and verify their identities during a digital transaction.   Results from these investigations suggest that these mechanisms can make digital transactions privacy-friendly and secure while at the same time delivering convenience and usability for ordinary users.