Medicare Eligibility Assessment

Find Out If You Can Enroll in Medicare Right Now

Not sure if you’re eligible — or if a life change has opened an enrollment window? This questionnaire walks you through the questions that determine your Medicare eligibility and whether a Special Enrollment Period applies to your situation.

This assessment takes about 3–5 minutes and covers initial eligibility, work history, and life changes that may open an enrollment window.

What About Annual Enrollment & Open Enrollment?

During the Annual Enrollment Period (AEP) — October 15 through December 7 each year — everyone with Medicare is eligible to enroll in, switch, or drop a Medicare Advantage (MA), Medicare Advantage with Prescription Drug (MA-PD), or stand-alone Part D (PDP) plan. No special qualifying event is needed.

What About Medicare Supplement (Medigap)?

You can apply for a Medicare Supplement plan at any time during the year — Supplements are not restricted to AEP. However, outside of your one-time Medigap Open Enrollment Period (the 6-month window starting when you are 65+ and enrolled in Part B), you will need to pass medical underwriting to be approved.

This means an insurance company can review your health history and may deny coverage, charge higher premiums, or exclude pre-existing conditions based on your medical background. Some states (such as Florida, Indiana, and Illinois) offer additional guaranteed issue protections — but in most states, once your initial 6-month Medigap window closes, underwriting applies.

Bottom line: If you’re thinking about switching from Medicare Advantage to a Supplement, you can do so — but approval is not guaranteed. The earlier you apply, the better your chances of qualifying.

This questionnaire focuses on determining your initial Medicare eligibility and whether a Special Enrollment Period (SEP) applies to you for Medicare Advantage, Part D, and Part B enrollment.

Section 1 of 4

Section 1: Basic Eligibility

Question 1

How old are you?

Question 2

What is your citizenship or residency status?

Question 3

Are you currently receiving Social Security Disability Insurance (SSDI) benefits?

Question 4

Have you been diagnosed with either of the following?

Question 5

Have you (or your current/former spouse) worked and paid Medicare taxes for at least 10 years (40 quarters)?

This determines whether you qualify for premium-free Part A.

Question 6

Are you currently receiving Social Security retirement benefits?

This determines whether you’ll be automatically enrolled in Parts A and B at 65.

Question 7

What is your current health insurance situation?

Select the option that best describes your primary coverage today.

Question 8

How many employees does your (or your spouse’s) employer have?

This is critical — it determines whether your employer plan or Medicare is primary.

Question 9

Which parts of Medicare do you currently have?

Select all that apply.

Question 10

Have any of the following happened to you in the last 12 months — or will they happen in the next 2 months?

Select ALL that apply. These life changes may trigger a Special Enrollment Period.

Question 11

Have you involuntarily lost prescription drug coverage in the last 63 days — or will you lose it within the next 63 days?

This includes employer drug plans, union drug plans, VA drug benefits, or any other coverage that was “creditable” — meaning it was at least as good as Medicare Part D. Losing creditable drug coverage opens a Special Enrollment Period to join a Part D or Medicare Advantage drug plan without penalty.

Question 12

Are you interested in switching to a Medicare Advantage or Part D plan that has a 5-star quality rating from Medicare?

A 5-star SEP allows you to switch to a top-rated plan once per year, anytime.

Question 13

Do any of the following apply to you?

These may qualify you for a Special Needs Plan (SNP) with continuous enrollment rights.

Question 14

Are you currently contributing to a Health Savings Account (HSA)?

Enrolling in any part of Medicare makes you ineligible to contribute to an HSA.

Question 15

Is your current health coverage provided through a spouse’s employer?

Question 16

Did you previously decline or delay enrolling in Medicare Part B?

Question 17

When did the event that changed your coverage situation happen (or when will it happen)?

Think back to the life changes you selected earlier — losing employer coverage, moving, retiring, losing Medicaid, etc. When did that event occur? Most Special Enrollment Periods have strict deadlines (typically 60–63 days from the event), so timing is critical.

Learn More About Medicare

Understanding the rules before you enroll can prevent costly mistakes.

Disclaimer: This questionnaire is for educational and informational purposes only. It does not constitute legal, financial, or enrollment advice. Medicare eligibility rules are complex and subject to change. Individual circumstances may vary. Always verify your eligibility, enrollment periods, and coverage options with the Social Security Administration (1-800-772-1213), Medicare (1-800-MEDICARE), or a licensed Medicare agent before making any enrollment decisions. Eligry LLC is a licensed, independent insurance advisory firm.