Abstract: A system and method for generating and administering an insurance product e.g., an insurance policy and/or rider, via. a computer system, that reimburses a policy holder for the cost of health insurance administered under COBRA, by providing benefits that reimburse a policy holder for all or a portion of a policy holder's COBRA insurance premiums for a period of time. The policy holder may receive health benefits under their original group plan at his or her original employer-sponsored, group health plan rate, and have a portion of the cost reimbursed through the insurance product, or the policy holder may elect to receive individual/family health insurance coverage, where the policy holder is instead reimbursed for all or a portion of the premiums for that coverage for a period of time by the insurance product.