This session demos using Desired State Configuration (DSC) with Release Management Online (RMO) for Visual Studio Online (VSO) to tackle real-world deployment challenges to the cloud via Azure. We start by presenting an overview of the key concepts, architecture, and configuration of the various components. We discuss the out-of-the box deployment actions available to compose automations for common deployment scenarios and how to use extensibility to cover the not-so-common scenarios. In more detail, we discuss adding custom DSC resources, how to trigger release as part of a build and how to leverage logs to diagnose failed releases. These are presented through specific scenarios encountered in the field.