An automated system allows users to request one or more insurance quotes through a self-service and/or agent-service communication channel. The system includes an interface that may receive user data from a remote or local system or application. A front-end application or system selectively passes a user's data to a record keeping system. A quote server or a quote processor generates one or more insurance quotes that are customized to the user's price and/or coverage preferences. A recommendation engine recommends one or more insurance coverages based on the information known about that user and in some instances, based on information known about others. The recommendation engine may call attention to selected insurance coverages that do not include a coverage feature or match a recommended coverage level.