In 2014, Microsoft announced a partnership with Docker to integrate Docker's open-source container technology into Windows Server, allowing developers to create distributed, container-based applications compatible with various programming languages, including .NET. This integration is set to offer significant benefits, such as improved application isolation and resource efficiency compared to traditional virtual machines. The article explores potential deployment strategies using Docker with Octopus Deploy, a deployment automation tool, highlighting different approaches like treating Docker as an infrastructure concern, building new images per deployment, or creating images per release to maintain consistency across environments. While Docker simplifies application packaging and deployment, Octopus continues to provide orchestration capabilities for managing complex deployment processes. The discussion also addresses the potential impact of Docker on Azure cloud service projects and the evolving ecosystem of Windows Server with Docker support.