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Medicare guidance

Medicare Enrollment Periods: When to Sign Up or Change Coverage

Choose the path that matches the coverage you need to start or change. Parts A and B, Medicare Advantage, Part D and Medigap do not share one universal enrollment window.

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Medicare Enrollment Guides: a roadmap leading from a calendar and retirement folder to Medicare coverage choices.

What Brings You Here?

I’m turning 65

Start with enrollment timing and your first coverage decisions.

I’m retiring or leaving employer coverage

Coordinate Medicare with the date your employer coverage ends.

I want to review my coverage

Recheck doctors, medicines, pharmacies and total costs.

I need help with a coverage problem

Find help with a bill, a denial, a provider change or a lost card.

I missed my Part B sign-up window — review the General Enrollment Period, possible Special Enrollment Periods and penalty rules.

Getting Medicare before age 65? Start here.

First identify the coverage—then the enrollment period.

Use the first-time guides for Medicare Parts A and B. Use the working and retirement guides when employer coverage changes that timeline. If you already have Medicare, use the annual, Medicare Advantage Open Enrollment or Special Enrollment Period guides for the specific plan change you are considering.

VA health care, TRICARE For Life and CHAMPVA have distinct Part B and coordination rules. Use the Veterans and Medicare hub before treating military or veterans coverage like an employer plan.

Enrollment Path

Start Here

Turning 65? Here Is How to Prepare for Medicare The complete overview of Parts A and B, employer coverage and private-plan choices. Turning 65 Medicare Checklist A six-month planning timeline for coverage, HSA and household decisions. When Should You Sign Up for Medicare Parts A and B? Compare Initial, working-aged Special and General Enrollment Periods for Original Medicare. Medicare Initial Enrollment Period Calculate the seven-month window and coverage start date. Medicare Under 65 Understand disability, SSDI, ALS and ESRD eligibility before age 65.
Enrollment Path

First-Time Parts A and B Enrollment

How to Enroll in Medicare Parts A and B Choose the correct Social Security application route. Automatic Medicare Enrollment at 65 Learn whether a card should arrive or you must apply. Part B Special Enrollment Period Forms Understand CMS-40B, CMS-L564 and the eight-month clock. Part B Late Enrollment Penalty Review the 10% rule and General Enrollment Period. Part D Late Enrollment Penalty Understand creditable drug coverage, uncovered months and how the penalty is calculated.
Enrollment Path

Working, Retiring and Other Coverage

Can I Delay Medicare While Working Past 65? Check active employment, payer order and HSA consequences. Medicare and the 20-Employee Rule Determine whether Medicare or the employer plan generally pays first. Retiring After 65 Coordinate the employer plan end date with Medicare. Medicare and HSA Rules Coordinate eligible months, deposits and possible retroactive Part A. COBRA and Medicare Do not let continuation coverage set the wrong Part B clock. Marketplace Coverage to Medicare Coordinate premium tax credits and household coverage. Spouse Health Insurance After Retirement Plan separate coverage for each spouse.
Enrollment Path

Annual Medicare Advantage and Part D Changes

Medicare Annual Enrollment Period Review October 15–December 7 Medicare Advantage and Part D changes for January 1. Annual Medicare Plan Review Recheck doctors, prescriptions, pharmacies, costs and plan rules before renewing. Medicare AEP in Springfield, Missouri Apply Annual Enrollment timing and review steps to local coverage decisions. Medicare Advantage Open Enrollment Period Learn who can make one limited Medicare Advantage change from January 1 through March 31.
Enrollment Path

Special Enrollment Periods and Coverage Events

Medicare Special Enrollment Periods Start here for employer coverage loss, moves, plan changes, Medicaid changes and other qualifying events. Moving With Medicare Separate a permanent residence change from travel and confirm service-area election rights. Medicare Advantage Plan Ending Review replacement options, deadlines and any guaranteed-issue protections. D-SNP Enrollment Periods Understand how Medicare and Medicaid eligibility can affect D-SNP enrollment.
Related Timing

Medigap Enrollment Is Different

Medigap Open Enrollment Period Learn about the federal six-month window tied to age 65 or older and Part B—not the fall AEP. Medigap Guaranteed-Issue Rights Review events that may protect access to certain Medicare Supplement plans.
Enrollment Path

Special and Local Situations

Already on Medicare Before 65? Understand what changes when disability beneficiaries turn 65. Turning 65 in Springfield, Missouri Apply the enrollment checklist to Springfield providers and coverage. Turning 65 in Texas County, Missouri Plan around rural providers, pharmacies and travel distance.
Four Questions

What Determines Your Medicare Timeline?

Will enrollment be automatic?

Your Social Security or Railroad Retirement status can determine whether a card arrives automatically.

Read the automatic enrollment guide →

What coverage do you have?

Current-employment group coverage is treated differently from COBRA, retiree or Marketplace coverage.

Compare coverage types →

Who pays first?

Employer size and the reason for Medicare eligibility affect coordination.

Review the payer rules →

Who else depends on the plan?

A spouse or dependent may need separate coverage when the employee moves to Medicare.

Plan coverage for a spouse →
Before Making a Change

Information to Gather

  • Your expected retirement and coverage-end dates.
  • Whether coverage is based on current employment.
  • The employer’s official Medicare coordination size.
  • Your Social Security or Railroad Retirement status.
  • Any HSA contributions by you or the employer.
  • Doctors, facilities, prescriptions and pharmacies.
  • The spouse or dependents who need replacement coverage.
Common Questions

Frequently Asked Questions

When should I begin preparing for Medicare?

Begin at least three months before the desired start date. Six months gives more time when employer coverage, an HSA, retirement or a spouse’s coverage is involved.

Does everyone automatically receive Medicare at 65?

No. Automatic enrollment generally depends on receiving qualifying Social Security or Railroad Retirement benefits before age 65.

Can I delay Medicare because I am still working?

Possibly, when you have qualifying group coverage based on current employment. Employer size and payer order must also be confirmed.

Does COBRA extend my Part B enrollment period?

No. COBRA does not extend the working-aged Part B Special Enrollment Period.

Can Marketplace coverage replace Medicare at 65?

Most people eligible for premium-free Part A should enroll in Medicare and generally lose eligibility for Marketplace financial assistance for their own coverage.

Do I need to stop HSA contributions?

Medicare-covered months provide no HSA contribution allowance. A deposit for earlier eligible months may still be allowed by the applicable tax filing deadline if unused annual contribution room remains. Plan ahead: retroactive premium-free Part A can reduce that room, and Medicare generally advises stopping contributions six months before retiring or applying for Social Security or Railroad Retirement benefits.

Can Thompson Medicare Brokerage enroll me in Parts A and B?

No. Social Security or the Railroad Retirement Board handles Parts A and B. We help compare the private Medicare coverage choices that follow.

Enrollment and Turning 65

Enrollment hub · You are hereMedicare Enrollment and Turning 65
Pillar guideTurning 65? Here Is How to Prepare for MedicarePlanning guideTurning 65 Medicare ChecklistTiming guideWhen Should You Sign Up for Medicare?Enrollment windowMedicare Initial Enrollment PeriodUnder-65 eligibilityMedicare Under 65: Disability, SSDI, ALS and ESRDRelated guideSigning Up for Medicare With Railroad Retirement BenefitsRelated guideI Enrolled in Medicare—What Happens Next?

More Medicare guidance

Related Articles

Related articleOriginal Medicare Parts A and BRelated articleVeterans and Medicare hubRelated articleHow to Enroll in Medicare Parts A and B Choose the correct Social Security application route.Related articleAutomatic Medicare Enrollment at 65 Learn whether a card should arrive or you must apply.State-specific enrollmentTurning 65 in Illinois

Independent Medicare guidance

Build the Enrollment Path Around Your Actual Coverage

Benjamin Thompson can help people in Missouri and Illinois compare the private Medicare options represented by Thompson Medicare Brokerage and organize the questions to take to Social Security, employers, the Marketplace or a tax professional.

Schedule a No-Cost ConsultationCall (855) 982-6525

Thompson Medicare Brokerage is not connected with or endorsed by the U.S. government or the federal Medicare program. This resource center provides general educational information. Official enrollment, effective-date, coordination and tax decisions depend on the individual situation.