We Help You Know
Where to Start
When Looking at Medicare
This Medicare Enrollment Guide breaks down everything you need to know to get started with Medicare simply, clearly, and without the confusion.
Get guidance on the first steps to explore your Medicare options.
Understand your choices and how employer coverage may impact enrollment.
Learn the enrollment process, timelines, and important information.
Compare Medicare coverage choices to find the right fit for you.
Get clarity on Medicare costs and how to plan for your healthcare expenses.
Where to Start With Medicare
A Licensed Advisor’s Step-by-Step Guide
Step 1
Establish which Group You are in?
Are you…
Group 1
Turning 65 & keeping employer coverage
Group 2
Turning 65 & dropping employer coverage
Group 3
Turning 65 & unemployed
Group 4
Over 65, retiring & losing employer coverage
Step 2
follow your specific GROUP’s Action Plan
Group 1: Turning 65 & Still Employed (Wants to KEEP employer health coverage)
If you or your spouse are still working and have active group health insurance, you are in a unique position. You may be able to delay Medicare without paying any late-enrollment penalties down the road.
Action Plan
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Group 2: Turning 65 & Still Employed (Wants to DROP employer coverage or HAS NO coverage)
Even if you plan to keep working, you are not obligated to stay on your company’s health insurance—especially if the employee contributions or deductibles are high.
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Action Plan
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Mark Your Initial Enrollment Period (IEP): You have a 7-month window to sign up: the 3 months before your birth month, your birth month, and the 3 months after.
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Apply for Parts A & B via Social Security: If you aren't collecting Social Security benefits yet, enrollment isn't automatic. Submit your application online at SSA.gov(opens in new tab) 2 to 3 months before your 65th birthday month.
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Select Your Coverage Path (Before Your Effective Date): Decide between Original Medicare + Medigap + Part D (maximum provider freedom) or Medicare Advantage / Part C (bundled managed care). Secure this coverage before your active employer insurance drops to ensure zero gap in protection.
Group 3: Turning 65 & Not Employed
If you are retired, self-employed without group coverage, or between jobs as you approach 65, enrolling in Medicare on time is critical to prevent lifelong late-enrollment penalties.
Action Plan
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Verify Automatic vs. Manual Enrollment:
- Taking Social Security already? You should automatically receive your Red, White, and Blue Medicare card in the mail about 3 months before your 65th birthday.
- Not taking Social Security yet? You must actively enroll in Parts A and B via SSA.gov during your 7-month IEP window.
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Avoid the Part D Drug Penalty: Even if you take zero prescription medications, you must maintain "creditable coverage." If you skip Part D or a plan with built-in drug coverage, Medicare assesses a permanent 1% per month penalty for every month you delay.
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Lock in Your Medigap Open Enrollment Rights: When your Part B goes active at 65, a 6-month Medigap Open Enrollment Period begins. During these 6 months, insurance companies cannot deny you coverage or raise your rates due to pre-existing conditions.
Group 4: Over 65, Retiring, and Losing Employer Health
coverage and are now preparing to retire, you get a special window to transition onto Medicare cleanly without penalties.
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Action Plan
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Trigger Your Special Enrollment Period (SEP): You have an 8-month Special Enrollment Period starting the month after your active employment or group coverage ends (whichever happens first). Note: COBRA or retiree coverage does NOT count as active coverage.
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Submit the Required Government Forms: To enroll in Part B after age 65 without penalty, you must submit two forms to Social Security:
- Form CMS-40B: Your application for Medicare Part B.
- Form CMS-L564: Completed by your employer to prove you had continuous, creditable health coverage since turning 65.
***PLEASE NOTE: We walk provide you with forms and walk you through entire process.
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Watch the HSA Backdate Rule: When enrolling in Medicare Part A after age 65, Medicare automatically backdates your Part A start date by up to 6 months. Stop all HSA contributions at least 6 months prior to applying for Part A to avoid IRS tax penalties.
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Decide on Original Medicare vs. Medicare Advantage: The Two Paths: Once you establish your enrollment timeline, you must choose how you want to receive your benefits:
Last Medically & Regulatory Reviewed: July 2026
Frequently Asked Questions
If you miss your IEP and do not qualify for a Special Enrollment Period (Group 4), you must wait for the General Enrollment Period (January 1 – March 31). Coverage begins the month after you sign up, and you may face a lifetime 10% Part B late penalty for every 12-month period you were eligible but un-enrolled.
Part A is premium-free for anyone who (or whose spouse) paid Medicare taxes through payroll for at least 10 years (40 quarters). Part B carries a standard monthly premium determined annually by the federal government(See IRMAA Chart.)
Credentials
Written by: MediPlans NJ
Credentials: Licensed Independent Health & Medicare Insurance Advisors
Location: Cherry Hill, New Jersey
Editorial Integrity: This guide is published in compliance with CMS guidelines. MediPlans NJ provides independent, unbiased comparisons across Medicare Advantage, Medigap, and Part D plans to help consumers make confident decisions.