A data processing system for machine-learning driven data analysis and reminders implements obtaining an electronic copy of demographic information and an electronic copy of insurance and benefits information associated with a user; providing the demographic information and the insurance and benefits information to a first machine learning model; analyzing the demographic information and the insurance and benefits information with the first machine learning model to output a first benefits utilization prediction that the one or more benefits are available to the user; providing the first benefits utilization prediction as an input to a recommendation engine; generating, using the recommendation engine, a benefits usage summary recommendation report that presents the information regarding the one or more benefits available to the user based on the first benefits utilization prediction; and causing a user interface of a display of a computing device to present the benefits usage summary recommendation report.