A skill-based bonusing interleaved wagering system is disclosed, including an interactive controller configured to: communicate application telemetry; receive a wager outcome; receive an application resource; initiate a portion of the interactive controller that provides the bonus goal; communicate additional application telemetry; receive and display bonus wager outcome; a wager controller constructed to: receive the wager request; determine a wager outcome; communicate the wager outcome; receive bonus wager request; determine a bonus wager outcome; and communicate bonus wager outcome; and the application controller operatively connecting the interactive controller and the wager controller, the application controller constructed to: receive application telemetry; determine whether to trigger a wager; communicating wager request; receive and communicate the wager outcome; determine and communicate the application resource; communicate a bonus goal offer; receive additional application telemetry; determine whether the bonus goal is achieved; generate and communicate bonus wager request; communicate the bonus wager outcome.