A recommendation module interleaved wagering system is disclosed, including an interactive processing device constructed to: receive recommendation data; display one or more recommendations; communicate selection data and application telemetry data; receive wagering telemetry and application resource data; configure a wagering user interface; and incorporate the application resource data; wager controller constructed to: communicate user wager data; receive wager request data; determine and communicate wager outcome; recommendation module constructed to: receive recommendation request data; receive user wager data; determine recommendations; and communicate recommendation data; process controller operatively connecting interactive processing device and wager controller, constructed to: communicate recommendation request data; receive recommendation data; communicate recommendation data; receive selection data; receive application telemetry data; determine whether to trigger wager request; generate wager request data; communicate wager request data; receive wager outcome data; communicate wagering telemetry data and application resource data.