Mandy Kloppers

5 Insurance Deadlines Seniors Should Know Before Retirement

Most Americans become eligible for Medicare enrollment in a seven-month window surrounding their 65th birthday. While many continue to work (and keep their private health insurance), enrolling for the national health insurance program during this time is crucial. Otherwise, you could pay a late enrollment fee or find yourself without coverage if something were to happen to your existing plan. Here are five insurance deadlines seniors should make note of as they approach retirement. 

1.  Medicare Parts A and B  

Those who receive Social Security benefits at least four months before they turn 65 automatically become enrolled in Medicare Parts A and B (inpatient and outpatient coverage). You should receive a letter from Social Security that mentions your policy information, which includes your new insurance card. Depending on your health requirements and if you have private health insurance, you may only require Part A. Either way, still be sure to apply for Medicarewithin your initial enrollment period. If you miss this 7-month window surrounding your 65th birthday, you can still apply for benefits but may be charged a penalty fee. 

2. Medicare Part D

Medicare Part D offers coverage for prescription drugs, and enrollment requirements fall within the same 7-month enrollment period surrounding your 65th birthday. You don’t get automatic coverage if you’ve received Social Security, so you’ll need to apply for coverage online if you want this extra benefit. If you fail to sign up 63 days after the first enrollment period date, you may pay a late penalty for this coverage. Instead of following a late annual fee, it’s calculated from the number of months you didn’t have drug coverage by 1% of the current national beneficiary premium, according to You must sign up in advance since the penalty is applied to your premium and stays tacked on whenever the national beneficiary premium rises. 

3. Medicare Supplement Insurance Plan

If you have two separate health insurance providers sharing expenses (Medicare and private health insurance), or if Medicare doesn’t cover specific health services, you can sign up for a Medicare Supplement Insurance Plan. The enrollment period lasts six months and begins when you turn 65. By law, your private health insurance company must sell you a Supplement Plan no matter the condition of your health, but they’re free to charge more or deny you after the initial enrollment period ends. Essentially, it offers seniors a Medigap plan without any significant changes to their coverage.  

4. Medicare Open Enrollment  

Medicare Open Enrollment offers seniors a chance to make changes to their current Medicare coverage plan without any penalties. You can make adjustments anywhere between October 15th and December 7th each year, which take effect the following year starting on January 1st. During this time you can choose to drop or join a Medicare Advantage Plan, change your Medicare Part D plan, or return to basic Medicare coverage. 

5. Medicare Advantage Open Enrollment

Only seniors who already have a Medicare Advantage Plan should worry about this open enrollment period since it allows you to make adjustments to your plan. However, you can also return to basic Medicare coverage or purchase a Medicare Part D plan during this time if you so choose. The enrollment period lasts from January 1st and ends on March 31st each year. On the first of the month, after your request is received, your new plan will take effect, and you can only make a change once during this period.  

With proper preparation and planning, applying for Medicare (and managing its many deadlines!) can help set you up for insurance success in your later years.