In some implementations, a system adaptively adapts engagement between a user and an application based on prior user interactions and context data associated with the user. A performance category for which performance is tracked for a user of the application is initially identified. Context data indicating a current context of the user is received from a client device associated with the user. One or more responsiveness scores indicating actions of the user with respect to the performance category following the previous communications through the application are determined. A communication is then selected from among communications of multiple types based on the context data for the user and the one or more responsiveness scores for the user. A time to provide the communication to the user is determined based on the context data. The selected communication is provided for output by the client device at the determined time.