We worked to automate the build-and-deploy process for our Windows agent using a combination of tools including Jenkins, Ansible, Powershell, and WinRM. Our goal was to cover four essential steps: building the agent installer, deploying it to canary machines, running tests on those machines, and releasing the installer. We used Ansible to automate these tasks by leveraging its existing support for Windows and our team's existing use of it for provisioning machines. Powershell was chosen as a complementary tool for remote access and deployment. After overcoming the initial challenge of introducing new technologies to the team, we successfully reduced the release time of our Windows agent from a half-day manual process to a five-minute Jenkins job.