Systems and methods for managing deployment of an update to computing devices, and for diagnosing issues with such deployment, are provided. An update deployment manager determines one or more initial computing devices to receive and execute an update. The update deployment manager further monitors a set of performance metrics with respect to the initial computing devices or a collection of computing devices. If a deployment issue is detected based on the monitored metrics, the update deployment manager may attempt to diagnosis the deployment issue. For example, the update deployment manager may determine that a specific characteristic of computing devices is associated with the deployment issue. Thereafter, the update deployment manager may modify future deployment based on the diagnosis (e.g., to exclude computing devices likely to experience the deployment issue).