Turning 65
Turning 65? Start With Medicare Education — Not a Sales Pitch.
Here is a plain-English, month-by-month checklist so you understand your timing, your options, and the questions worth asking before choosing a Medicare Supplement plan.
Month by month
Your Turning 65 checklist
- 1
6 months before your birthday month
- Confirm your Medicare eligibility date — generally the first day of the month you turn 65.
- Decide whether you will keep employer coverage or move fully to Medicare.
- Learn the difference between Original Medicare + Medigap and Medicare Advantage.
- 2
3 months before (Initial Enrollment Period opens)
- Your 7-month Initial Enrollment Period generally begins 3 months before your birthday month.
- Enroll in Part A (hospital) and Part B (medical) if you are not receiving Social Security yet.
- Begin comparing Medigap plan letters — Plan G and Plan N are the most common starting points.
- 3
1–2 months before
- Review a Part D prescription drug plan that fits your medications.
- Ask for Medigap illustrations from a licensed agent — rate history and rating method matter.
- Prepare your Medicare number and Part B effective date for the application.
- 4
Your birthday month (Part B effective)
- Your 6-month Medigap Open Enrollment Period generally starts once you are 65 and enrolled in Part B.
- During this window, carriers generally cannot use health questions to decline or rate you.
- Apply for the Medigap plan you chose so coverage begins alongside Part B.
- 5
After coverage starts
- Keep your Medicare card and Medigap ID card together.
- Set a yearly reminder to review your Part D plan during the fall Annual Enrollment Period.
- Reach out with questions — a good agent is a resource for years, not just at enrollment.
Key terms
What each piece means
Medicare Part A
Hospital insurance. Usually premium-free if you or a spouse paid Medicare taxes for 10+ years.
Medicare Part B
Medical insurance. Has a monthly premium and generally covers 80% of approved costs after the deductible.
Initial Enrollment Period
The 7-month window around your 65th birthday to enroll in Part A and Part B.
Medicare Supplement Open Enrollment
Generally 6 months from your Part B effective date at 65+. Protected window for Medigap.
Prescription coverage
Medigap does not include drug coverage — a separate Part D plan is typically used.
Medicare Advantage distinction
A different approach that replaces how you receive Medicare benefits. Medigap works with Original Medicare instead.
Medigap timing
Applying inside a protected window may avoid medical underwriting, subject to applicable rules.
Questions to ask an agent
Rate history, rating method (attained/issue/community), household discounts, and carrier stability.
2-minute tool
Medicare Supplement Fit Check
Seven quick questions that help you understand which Medigap topics matter most for your situation. Educational only — not a recommendation.
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This is an educational insurance consultation. We can discuss Medicare Supplement options available in your state and your individual circumstances. No pressure, no obligation.
This page provides general educational information and is not a recommendation or guarantee of eligibility, approval, coverage, or premium. Medigap availability, premiums, underwriting, and enrollment rights can vary by state, carrier, and individual circumstances and are subject to applicable rules. Gilbert Services Southwest is not affiliated with or endorsed by Medicare, CMS, or the federal government. This is a solicitation for insurance.