Over the past year, GitHub has faced challenges in adapting its deployment processes to accommodate a doubling of developers contributing to its core application, leading to issues with its existing chatops-based deployment tooling. The previous system, which relied on a single Slack channel to manage and track deployments, became overwhelmed and confusing due to the high volume of messages, thereby increasing the risk and reducing efficiency. To address these issues, GitHub revamped its deployment system by introducing two canary stages, with the first at 2% and a second at 20% deployment traffic, to better identify potential issues before full production rollout. Additionally, the entire deployment process was automated to allow for a single command to handle multiple deployment stages, streamlining the process with automated progression and time-gated checks. This new system is backed by a state-machine model and features a UI component for better tracking and monitoring, significantly improving developer experience and system reliability. The improvements have been well received internally and have influenced GitHub's broader offerings, including the GitHub Actions CD, demonstrating the success of the deployment team's collaborative efforts.