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How to Sign Up for Medicare: A Retiree’s Complete Guide

by Christine Corsini | Jul 3, 2025 | Medicare medical savings account | 0 comments

Happy retired couple relaxing on patio with coffee and tablet, exploring how to sign up for Medicare during retirement.

Retiring soon means it’s time to understand how to sign up for Medicare—and getting this right protects you from costly penalties and coverage gaps.

Happy retired couple relaxing on patio with coffee and tablet, exploring how to sign up for Medicare during retirement.

Key Takeaways

  • Start planning 3 months before your 65th birthday to avoid enrollment penalties and coverage gaps.
  • Medicare enrollment happens through Social Security online, by phone, or in person with required documents.
  • Original Medicare (Parts A & B) covers basics but leaves significant gaps requiring additional coverage.
  • Timing matters critically when transitioning from employer coverage to Medicare.
  • Late enrollment penalties can cost hundreds annually for the rest of your Medicare coverage.
  • Expert guidance helps navigate options and ensures you choose the right Medicare path for your needs.

When to Start Thinking About Medicare Enrollment

Your Medicare journey begins 3 months before your 65th birthday.

The Initial Enrollment Period (IEP) runs for 7 months total: 3 months before your birthday month, your birthday month, and 3 months after. If you’re working past 65 with employer coverage, you may qualify for a Special Enrollment Period when you retire.

Note that Medicare open enrollment (October 15 – December 7) is different from your Initial Enrollment Period and applies to changing existing Medicare coverage.

Get a Free Medicare Supplement Quote


How to Sign Up for Medicare

Medicare enrollment happens through Social Security, not Medicare.gov directly.

You have three enrollment options:

  • Online at ssa.gov (fastest option)
  • Call 1-800-772-1213
  • Visit your local Social Security office

Required documents include:

  • Social Security card
  • Birth certificate
  • Current health coverage information

Need help navigating your Medicare options? Contact one of our Personal Benefits Managers for free enrollment guidance tailored to your specific situation.

What Each Part of Medicare Covers

Understanding Medicare’s four parts helps you make informed coverage decisions.

  • Part A covers hospital stays and skilled nursing facility care
  • Part B covers doctor visits, preventive care, and outpatient services
  • Part C (Medicare Advantage) combines Parts A and B with private insurance
  • Part D provides prescription drug coverage

Original Medicare (Parts A & B) doesn’t cover:

  • Dental care
  • Vision care
  • Long-term care

Learn more about Medicare Part D prescription coverage.

Avoiding Penalties and Coverage Gaps

The Part B late enrollment penalty is permanent and expensive.

Key penalty facts:

  • 10% penalty for each year you delay enrollment without creditable coverage
  • Penalty continues for life
  • Creditable coverage includes most employer group plans and COBRA

Special Enrollment Periods allow penalty-free enrollment when you lose employer coverage, but you must act within 8 months.

Get a Free Medicare Advantage Quote

Select whether you would like quotes on Medicare Advantage and MAPD plans, or Part D prescription plans.


Why Medigap or Medicare Advantage Matters

Original Medicare’s gaps can create financial hardship without additional coverage.

Your supplemental coverage options:

  • Medigap plans work with Original Medicare to cover copays and deductibles.
  • Medicare Advantage plans replace Original Medicare with private insurance that often includes dental and vision.
  • Medi-Share 65+ offers faith-based health sharing as an alternative to traditional Medicare supplements

Frequently Asked Questions

Q: Can I sign up for Medicare if I’m still working at 65? 

A: Yes, but you may not need to if you have creditable employer coverage. Consult with HR and a Medicare advisor to determine the best timing.

Q: What happens if I miss my Initial Enrollment Period? 

A: You’ll face late enrollment penalties and may need to wait until the next General Enrollment Period (January-March) for coverage starting July 1st.

Q: Do I automatically get Medicare when I turn 65? 

A: Only if you’re already receiving Social Security benefits. Otherwise, you must actively enroll during your Initial Enrollment Period.

Make Your Medicare Transition Seamless

How to sign up for Medicare doesn’t have to be overwhelming when you have the right guidance and timing.

Starting your Medicare planning 3 months before your 65th birthday gives you time to understand your options, avoid penalties, and ensure seamless coverage. Whether you choose Original Medicare with a Medigap plan or Medicare Advantage, the key is making an informed decision based on your specific needs and circumstances.

Don’t navigate Medicare enrollment alone. Our Personal Benefits Managers specialize in helping retirees understand their Medicare options and make confident choices. Schedule a free consultation with one of our Medicare Personal Benefits Managers today to get personalized enrollment help and ensure you’re making the best Medicare decisions for your retirement.

For Further Reading:

  • MediShare 65+ Health Sharing Program vs. MediGap Plan G
  • Medicare Flex Card: Your Guide to Everything Seniors Need to Know
  • Maximum Out-of-Pocket for Medicare Plans
Christine Corsini

Christine Corsini is one of your Personal Benefits Managers at MediGap Advisors. She loves working for Medigap Advisors especially helping clients choose the right Medicare plan.

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Disclaimer: MediGap Advisors is not connected with or endorsed by the U.S. Government or the federal Medicare program. Medicare has neither reviewed nor endorsed the information contained on this website. This is not a complete listing of plans available in your service area. For a complete listing please contact 1-800-MEDICARE or consult www.medicare.gov (TTY users should call 1-877-486-2048), 24 hours a day/7 days a week.