Abstract: Technologies are disclosed for machine learning assisted automation of workflows based on observation of user interaction with operating system (OS) platform features. User interaction data is collected that defines the activity of a user with respect to platform features provided by an OS. The user interaction data is provided to a trained machine learning model that is configured to identify a workflow for performing a task based on the user interaction data. If the trained machine learning model identifies a relevant workflow, a user interface (UI) can be presented to the user that includes data identifying the workflow selected by the trained machine learning model. The UI can also include an element which, when selected, will cause the computing device to execute the workflow selected by the trained machine learning model based on the user interaction data.