Medicare Starter Guide: Your First 90 Days
Starting Medicare is one of the most important financial and health decisions you will make. The choices you make in your first 90 days can affect your coverage, your costs, and your flexibility for years.
This guide walks you through what to do, when to do it, and why it matters.
Before Day One: Know When Your Coverage Starts
Your Initial Enrollment Period (IEP) spans seven months: three months before the month you turn 65, the month you turn 65, and three months after.
- Enroll in the three months before your birthday month: coverage starts the month you turn 65
- Enroll in your birthday month: coverage starts one month later
- Enroll in the three months after: coverage starts two to three months after enrollment
If you are already receiving Social Security at 65, you are enrolled automatically. If not, enroll at SSA.gov or by calling 1-800-772-1213.
Still working with employer coverage? You may be able to delay Part B without Penalty. COBRA and retiree coverage do not count. See a licensed counselor before delaying.
Month 1: Confirm Your Coverage and Make Your First Big Decision
When your Medicare card arrives, confirm your Part A and Part B effective dates. Original Medicare alone leaves you exposed to significant out-of-pocket costs with no annual cap.
Medicare Supplement (Medigap): A Medicare Supplement fills in the out-of-pocket gaps left by Original Medicare. No networks. Any doctor or hospital that accepts Medicare accepts your coverage. Add a separate Part D plan for prescriptions.
Medicare Advantage (Part C): A private plan that replaces Original Medicare. Usually includes drug coverage. Often lower premiums but requires using a provider network.
Why this is time-sensitive: Your Medigap Open Enrollment Period opens the month you turn 65 AND are enrolled in Part B. It lasts exactly six months. During this window, insurers cannot reject you or charge more because of health conditions. After it closes, most states allow medical Underwriting. This window does not repeat. If you want a Medigap plan, apply during this period.
Month 1-2: Enroll in a Part D Prescription Drug Plan
Whether you choose Medigap or Medicare Advantage, you need Prescription Drug Coverage. If you choose Medigap, enroll in a standalone Part D plan separately. If you choose Medicare Advantage, most plans include drug coverage.
Do not skip Part D even if you take no medications. Going 63+ consecutive days without creditable drug coverage triggers the Part D late enrollment penalty: 1% of the national base beneficiary Premium ($38.99 in 2026) for every month you were without coverage, added permanently to your premium for life.
Month 2: Set Up Your Online Medicare Account
Create an account at MyMedicare.gov. This free portal gives you claims history, your Medicare Summary Notice, drug plan tools, and your Part D spending toward the $2,100 out-of-pocket cap (2026).
Month 2-3: Choose Your Doctors and Understand Your Coverage
Verify your providers accept your coverage. With Medigap, any Medicare-accepting doctor works. With Medicare Advantage, confirm providers are in-network.
Schedule a Welcome to Medicare visit. During the first 12 months of Part B coverage, you are entitled to a free preventive visit. Use it to establish care with a primary care provider.
Know your 2026 costs under Original Medicare:
- Part A Deductible: $1,736 per Benefit period
- Part B deductible: $283, then 20% Coinsurance
- Part D: insulin capped at $35/month; annual out-of-pocket cap $2,100
Month 3: Review and Confirm Everything Is Working
By end of your first 90 days, you should have: Medicare card with correct dates, Medigap or Medicare Advantage enrolled, Part D coverage in place, MyMedicare.gov set up, primary care provider established, Welcome to Medicare visit scheduled.
Check your first Medicare Summary Notice for services you did not receive, billing errors, or denied claims that should have been covered. Report issues to 1-800-MEDICARE.
Important Dates Going Forward
| Event | When |
|---|---|
| Medicare Open Enrollment | October 15 to December 7 each year |
| Medicare Advantage OEP | January 1 to March 31 each year |
| Annual Notice of Change | September (review plan changes for next year) |
| Part D cap resets | January 1 each year |
Your First 90 Days Checklist
- Confirm Part A and Part B effective dates
- Choose between Medigap and Medicare Advantage
- Apply for Medigap during your 6-month Open Enrollment Period
- Enroll in Part D or confirm drug coverage through Medicare Advantage
- Set up your MyMedicare.gov account
- Verify your doctors accept your coverage
- Schedule your Welcome to Medicare preventive visit
- Review your first Medicare Summary Notice for errors
Not sure where to start? A REMEDIGAP advisor can walk you through your options in plain English at no cost.
💡 Your next step: Once you have Medicare, most people add a supplement plan to cover out-of-pocket costs. Compare Medicare Supplement plans to find the right fit.
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Written by Michael Quinn
Licensed Broker, REMEDIGAP Founder
Fact Checked by Joann Quinn
Chief Compliance Officer
As a licensed insurance broker, REMEDIGAP upholds the principles of integrity in our editorial standards and ensures transparency in how we receive compensation from our insurance partners.