Digital transformation initiatives have impacted not only IT processes, but also cybersecurity and corporate compliance programs. Central to this transformation is the need to support and secure the use of a diverse portfolio of cloud applications. Enterprises with branch offices have been revisiting network infrastructure to support direct-to-cloud workflows, amplified by the increase in remote work. As employees work from distributed locations, access to a diverse range of applications data flows through egress points and through the edge direct to cloud stores. To protect data assets both in motion and at rest a modern approach to data loss prevention (DLP) designed for today’s digital enterprise is required. This paper explores the challenges associated with protecting data in the cloud era, the requirements of a contemporary solution, and how Palo Alto Network’s Enterprise DLP offering meets these requirements with a cloud-native implementation.