This chapter explores in more detail recent cases of data infringement and the problems which have resulted. The limitations of current regulatory models are considered and potential alternatives are discussed. The chapter demonstrates, the rise of digital data has presented new challenges that did not exist in an analogue world. Data on the lifestyle and health of individuals is particularly valuable to a range of stakeholders and presents difficult challenges for policymakers and regulators as they try to balance the broader needs of society with the protection of personal privacy. Both Google and Amazon have been involved in such projects with their expertise in handling data at scale as well as offering new ways to capture lifestyle data being seen by some policymakers in the NHS as being complementary to the aims of the health service.