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Jenkins Insurance & Retirement is a private insurance practice not affiliated with or endorsed by the U.S. government or the federal Medicare program.

Enroll On Your Own

How to Enroll in Medicare Yourself

You do not need an agent to enroll in Medicare. Every step below can be done on your own, for free, and this page walks through them in order — including the parts people most often get wrong.

First, the part that surprises people

Medicare isn't one sign-up — it's two decisions

Getting Medicare happens in two stages, handled by two different organizations. Missing that is the single most common reason people think they enrolled and later find out they didn't.

1. Original Medicare (Parts A and B)

Handled by Social Security — not Medicare, and not an insurance company.

This is the federal coverage itself. Most people pay $0 for Part A if they or a spouse worked 40+ quarters. Part B costs $202.90 a month in 2026 for most people, with a $283 annual deductible; higher earners pay more through IRMAA.

2. How you fill the gaps

Handled by private insurance companies.

Original Medicare alone has no drug coverage and no out-of-pocket limit. You close that either with a Medicare Advantage plan (Part C, usually with drug coverage built in) or by keeping Original Medicare and adding a Medigap policy plus a standalone Part D plan.

Step One

Are you already enrolled without doing anything?

If you're already receiving Social Security or Railroad Retirement benefits when you turn 65, Parts A and B start automatically — your card arrives about three months before your birthday month. If you are not drawing benefits yet, nothing happens on its own and you have to sign up.

  1. Go to ssa.gov/medicare and apply online — it takes about 10 minutes and is the fastest route.
  2. Or call Social Security at 1-800-772-1213 (TTY 1-800-325-0778), Monday–Friday.
  3. Or make an appointment at your local Social Security office.

Applying for Medicare is not the same as claiming Social Security retirement benefits. You can take Medicare at 65 and leave your retirement benefit to grow.

Step Two

Know which window you're in

WindowWhenWhat it lets you do
Initial Enrollment Period7 months around your 65th birthdayStarts 3 months before your birthday month, includes it, and runs 3 months after. Enrolling in the 3 months before means coverage starts the first of your birthday month.
General Enrollment PeriodJan 1 – Mar 31For anyone who missed their Initial Enrollment Period. Coverage begins the month after you enroll, and a late penalty may apply.
Medicare Open Enrollment (AEP)Oct 15 – Dec 7Join, switch, or drop a Medicare Advantage or Part D plan for the coming year. Changes take effect January 1.
Medicare Advantage Open EnrollmentJan 1 – Mar 31If you're already in a Medicare Advantage plan, you get one change — switch to a different Advantage plan or go back to Original Medicare.
Special Enrollment PeriodsVariesTriggered by events like leaving employer coverage, moving out of your plan's service area, or losing other creditable coverage.

Still covered by an employer group plan through your own or a spouse's active job? You may be able to delay Part B without penalty. This is the situation most worth a phone call before you act — the rules turn on the employer's size and whether the coverage counts as creditable.

Step Three

Compare plans and enroll

Once Parts A and B are in place, you pick the private coverage. You can do all of this yourself, in any of these places, at no cost:

Medicare Plan Finder (medicare.gov)

The official government tool. Shows every Medicare Advantage and Part D plan in your ZIP code, and lets you enter your prescriptions to see real yearly drug costs plan by plan. Nothing is more complete.

Open Plan Finder

Our plan finder

The same comparison tool we use with clients. It shows the Medicare Advantage and Part D plans we're contracted with in your county, and you can enroll straight through it. No appointment, no phone call.

Shop Medicare plans yourself

Buying a Medigap policy instead? Those are bought directly from the insurance company, not through Medicare. The timing matters more than anything else: during the 6-month Medigap Open Enrollment that starts the month you're both 65 and enrolled in Part B, an insurer cannot turn you down or charge you more for your health history. Outside that window, in Wyoming and Utah, they can.

Before You Start

What to have in front of you

  • Your Medicare number, once you have your card (or your Social Security number before that).
  • A current list of every prescription — exact names, doses, and how often you take them.
  • The names of the doctors, specialists, and hospitals you want to keep.
  • Your ZIP code and county — plan availability and pricing key on the county, not the state.
  • A rough sense of your yearly income, if you want to check whether IRMAA applies.

Honest Warnings

Where people get tripped up

Assuming Social Security enrolled you

If you weren't drawing benefits at 65, nothing happened automatically. People discover this months later, having gone uninsured in the meantime.

Skipping Part D because you take no drugs

The Part D late penalty is 1% of the national base premium for every month you went without creditable coverage, and it is permanent. A cheap plan now is usually cheaper than the penalty later.

Checking the premium but not the drug list

Two plans with the same premium can differ by thousands of dollars a year depending on which tier your prescriptions land in. The drug cost, not the premium, is usually the real number.

Assuming your doctor is in network

Medicare Advantage networks change every year. Confirm each provider for the specific plan and the specific plan year, not just the insurance company.

Missing the Medigap underwriting window

That 6-month guaranteed-issue window is the one Medicare deadline you cannot get back. After it, a Medigap insurer can decline you outright.

Free, Unbiased Help

If you want help that isn't us

We'd rather you got good information from someone else than bad information from nobody. All of these are free and none of them sell anything:

  • 1-800-MEDICARE

    1-800-633-4227, TTY 1-877-486-2048 — 24 hours a day, 7 days a week.

  • Medicare.gov

    The official program site, including Plan Finder and every plan document.

  • Wyoming SHIP

    Free counseling from your State Health Insurance Assistance Program.

  • Utah SHIP

    Free counseling through Utah's Aging and Adult Services.

Content reviewed against 2026 plan-year figures. Dollar amounts change annually — we'll confirm the current numbers in your consultation.

Enroll on your own — or ask first

Most people can do this themselves in an afternoon. If your situation has a wrinkle in it — employer coverage, a long prescription list, a Medigap health history — a free conversation costs you nothing and takes about 20 minutes.