Non-limiting examples of the present disclosure relate to generation and surfacing of user-specific contextual insights from analysis of telemetry data that is associated with user interaction with an exemplary application/service. Processing operations described herein extend to generation of any type of contextual insights from any type of telemetry data. In one example, user-specific contextual insights are generated to provide users with writing assistance to digital documents created through exemplary applications/services. A user interface is presented through a productivity service. Writing assistance telemetry data, associated with one or more users, is analyzed. Writing assistance telemetry data comprises, data evaluating, for the user(s), spelling, grammar and a writing style across content of one or more digital documents. User-specific insight analytics are generated for the user(s) based on analysis of the writing telemetry data. The user interface is adapted to present the generated user-specific contextual insights for the user.