Should You File for Social Security When You File for Medicare?

There are several reasons why enrolling in Medicare as soon as you're eligible is in your best interest—both for your finances and for your coverage options. It can be tempting to file for Social Security while enrolling in Medicare or right after Medicare enrollment, but a wrong choice could cost you tens of thousands of dollars.

Don’t Put Off Medicare Enrollment

There several reasons why you should enroll in Medicare as soon as you are eligible. There is only one reason you might want to delay enrollment.

If you are still working when you turn 65 and your employer offers a comparable or superior health plan, you can delay enrolling for Medicare while enrolled in your company plan. This also applies if you are covered under a spouse’s healthcare plan.

If you don’t have current coverage, then you should apply for Medicare as soon as you’re eligible. When you turn 65, you have a 7-month window to apply. The enrollment period begins three months before you turn 65, the month of your birthday, and three months after your 65th birthday. If you miss this enrollment period, you must wait for the annual Medicare open enrollment window of October 15th through December 7th.

Delaying Medicare enrollment has two serious penalties. The first is a lack of coverage. The longer you go without coverage, the more you are gambling with your health. Medicare A is free for most seniors and this covers stays in the hospital. Medicare B has a low monthly premium and includes an array of free preventive services and screenings, as well as doctor visits. Your long-term health prognosis depends on proactive healthcare strategies and Medicare provides those options for beneficiaries.

The second penalty you can incur from delayed Medicare enrollment is a financial one. A 10 percent increase will be assessed on your Medicare B premiums for each 12-month period—starting once you turn 66. A three-year delay could potentially see an increase of 30 percent on Medicare Part B premiums. This penalty is permanent!

Why You Might Want to Wait to File For Social Security

Social Security is the opposite of Medicare when it comes to financial penalties for your filing period. If you enroll in Medicare as soon as you become eligible, you are ensuring you don’t pay more for your premiums. If you file for Social Security as soon as you become eligible, you are taking a significant decrease in your maximum benefits.

Social Security retirement benefits are based on several factors, and the age that you file is one of the most important. If you file for Social Security at 65—the same time you file for Medicare—you will take a 13.34% decrease in full retirement age benefits if your full retirement age begins at 67.

However, there is more to consider. Social Security rewards filers who file beyond full retirement age. The maximum period one can postpone collection of benefits and receive an increase is 3 years. If you file for Social Security at age 70, you can maximize your full retirement benefits and collect 37.34% more than the amount you would collect if you had filed at 65. The year of your birth determines your full retirement age. Go here to learn your full retirement age and how benefits and penalties are applied to Social Security retirement benefits.

Figuring Out the Best Time to File for Social Security and Medicare For Your Unique Retirement Situation

Social Security and Medicare will play important roles in your retirement plan. Making your Medicare options and your Social Security benefits work together is critical if you want to maximize benefits, mitigate long-term health care concerns, and provide for optimal results for your retirement income. Use the Social Security calculator at the bottom of the page to get an estimate of your Social Security benefits.

If you would like to explore Medicare and long-term care options and/or see how Social Security fits in your retirement plan, Presidential provides free, no-obligation meetings and consultations. An hour of your time can save you tens of thousands of dollars in your retirement. Fill out the form or give us a call at 303-694-1600 with any questions or to set up a meeting.



The Presidential Wealth Management Social Security planning guide is filled with the core information we teach at our free educational workshops.

The guide is designed to explain the most common Social Security filing strategies and situations for individuals and couples.

Our workshops and educational materials were created to be shared with the community. If you would like a free copy of our guide, simply fill out the form below and we would be happy to send you a digital version through email or mail a printed copy to your home.


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