Peripheral device support with a digital assistant for operating system upgrades

A digital assistant supported across computing devices is configured to interact with an operating system (OS) upgrade system so that various user experiences, services, content, or features associated with support for peripheral devices during an OS upgrade of a computing device can be provided by the digital assistant and rendered as a native digital assistant user experience. The digital assistant is configured to surface a notification through a user interface (UI) when an OS upgrade is available for a user's computing device and recommended for installation. The OS upgrade system executes a confidence model in a machine learning system using real world crowd-sourced data to make predictions of successful post-upgrade operations of peripheral devices with an associated level of confidence. The digital assistant personalizes the OS upgrade notification to the user based on the configuration of computing and peripheral devices, applicable context, and the confidence level.