To explore what it meant to own and possess in the eighteenth century, Keeping Hold looks to instances in which people lost possessions and how they responded to such experiences. Chapter 2 begins the book’s focus on loss and does so by looking to urban sites. It looks to the city of the eighteenth century: London. The capital was of growing importance in this period as an economic powerhouse and social hub. Guidebooks emerged as an important genre for those seeking to comprehend London’s densely filled and ever-lengthening streets. The chapter explores these sources and finds how the capital was increasingly imagined as a site of deception and loss, where possessions might be pickpocketed or simply left in the bustle and in which servants and apprentices regularly ran away. The chapter examines how eighteenth-century Londoners responded to such perceived threats by utilising technologies of security, such as pockets and collars. By doing so they worked to prevent loss.