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.