Enroll in Medicare at 65
Turning 65 is a milestone—and the start of your Medicare journey. Enrolling at the right time helps you avoid penalties, coverage gaps, and costly mistakes. At Diversified Insurance Brokers, our licensed advisors make enrollment simple and align your choices (Original Medicare, Medigap, Medicare Advantage, Part D) with your doctors, prescriptions, and budget.
Compare Medicare Plans & Costs
Questions? Call 800-533-5969 or Book a call with Tonia (Medicare Advisor).
✅ When to Enroll (Initial Enrollment Period)
Your Initial Enrollment Period (IEP) is 7 months: the 3 months before your 65th birth month, your birth month, and the 3 months after.
- Enroll 1–3 months before 65: Coverage can start the month you turn 65.
- Enroll in your birth month: Coverage generally starts the following month.
- Enroll 1–3 months after: Coverage start can be delayed—avoid gaps if you can.
🧭 Still Working at 65? Know Your Path
- Employer has 20+ employees: You may delay Part B (and Part D) if your group plan is creditable. Keep proof for a Special Enrollment Period (SEP) later.
- Employer has fewer than 20 employees: Medicare is typically primary at 65—enroll in Part A and Part B to avoid coverage gaps.
- COBRA or retiree coverage: Usually not considered creditable for delaying Part B—review with an advisor before you decline Part B.
- HSA users: Stop HSA contributions up to 6 months before enrolling in Part A to avoid tax issues.
🧩 Your Medicare Building Blocks
- Part A: Hospital coverage (premium-free for most).
- Part B: Medical/doctor services (monthly premium; income-based adjustments may apply).
- Part D: Prescription drug plans (avoid late penalties with timely enrollment).
- Medigap (Supplement): Helps pay Part A & B costs; best time is your 6-month Medigap Open Enrollment window after Part B starts.
- Medicare Advantage (Part C): All-in-one alternative to Original Medicare, often with extra benefits and networks.
📝 Quick Enrollment Checklist
- Confirm whether you’ll retire or keep employer coverage at 65.
- Decide on Original Medicare + Medigap + Part D or Medicare Advantage.
- List doctors, hospitals, and prescriptions to ensure they’re covered.
- Check if your employer plan is creditable (drug & medical).
- Enroll during IEP (or SEP) to avoid late penalties.
💡 Example: Enrolling at 65 While Working
Linda turned 65 in April and kept large-employer coverage. We confirmed creditable status, delayed Part B without penalty, and later used her SEP to enroll in a Medigap + Part D combo when she retired—no late fees, no gaps.
Need Help Enrolling at 65?
Speak with a licensed Medicare advisor. We’ll compare plan options and handle enrollment for you.
FAQs: Enroll in Medicare at 65
When does my Initial Enrollment Period start and end?
Your IEP is 7 months total: the 3 months before your 65th birth month, your birth month, and the 3 months after.
Can I delay Part B if I’m still working?
Yes—if your employer (or spouse’s) plan is creditable and the employer has 20+ employees. Keep proof to use a Special Enrollment Period when coverage ends.
What if my employer has fewer than 20 employees?
Medicare usually becomes primary at 65. Enroll in Part A and Part B to avoid coordination issues and potential gaps.
Will I pay a penalty if I delay Part B?
There’s no penalty if you had creditable coverage and use your SEP. Without creditable coverage, a permanent Part B penalty may apply.
How does prescription coverage work at 65?
Enroll in a Part D plan during IEP (or SEP with creditable employer drug coverage) to avoid the Part D late enrollment penalty.
What’s the difference between Medigap and Medicare Advantage?
Medigap supplements Original Medicare and has no networks. Medicare Advantage is an alternative with networks and bundled benefits. We’ll compare both for your doctors and drugs.
When is my Medigap Open Enrollment?
Your 6-month Medigap window starts when Part B becomes effective—this is often the best time to enroll.
Can I keep contributing to an HSA?
Once Part A starts, you generally must stop HSA contributions (Part A can be retroactive up to 6 months). Plan ahead to avoid tax issues.
How do I enroll?
Apply online through SSA, by phone, or in person—then we’ll help you select Medigap/Part D or Medicare Advantage based on your needs.
About the Author:
Tonia Pettitt, CMIP©, is a seasoned Medicare specialist with more than 40 years of hands-on experience guiding individuals and families through the complexities of Medicare planning. As a senior advisor with the nationally licensed independent agency Diversified Insurance Brokers, Tonia provides clear, dependable guidance across all areas of Medicare—including Medicare Advantage, Medicare Supplement (Medigap), and Part D prescription coverage. Leveraging active contracts with dozens of highly rated insurance carriers, she helps clients compare options objectively and secure the most suitable coverage for their health and budget.
Known for her patient, education-first approach, Tonia has built a reputation as a trusted resource for retirees seeking reliable, unbiased Medicare support. With four decades of experience across evolving Medicare laws, carrier changes, and plan structures, she brings unmatched insight to every client conversation—ensuring clients feel confident, protected, and fully prepared for each stage of their retirement healthcare journey.
