When was the last time you really shopped for your health, dental, or vision plan? When was the last time you really shopped for your health, dental or vision plan? The five-year rule could change your retirement plans. To carry FEHB into retirement, even if you’ve had a long federal career, you generally must be enrolled in an FEHB plan for the five consecutive years right before retiring. And if you’ve never considered whether you’re overinsured, or if you’ve dismissed high-deductible health plans without taking a closer look, you should catch the full conversation.