A system and method provide supplemental insurance having a relatively high first deductible and relatively low first premiums when coverage begins. On the occurrence of a predetermined future event, such as a plan maturity date or other event, the first deductible decreases while maintaining a relatively low premium for the duration of the insurance plan for the policy owner. The policy owner may be provided with an option to elect, on a guaranteed basis, to reduce the first deductible amount to a lower deductible amount, in exchange for an increased premium amount, prior to the occurrence of the predetermined event. In some embodiments, the supplemental insurance is provided as a rider to a Medicare Supplement Plan F.