The Initial Enrollment Period at 65
Your first chance to sign up for Medicare lasts seven months: the three months before the month you turn 65, your birthday month, and the three months after. The same seven months are your first window to join a drug plan or a Medicare Advantage plan.
If you already collect Social Security or Railroad Retirement benefits at least four months before 65, you don’t need to act. You are enrolled in Parts A and B automatically, and your card arrives about three months before coverage starts. Everyone else applies through Social Security.
Premium-free Part A starts the month you turn 65, or the month before if your birthday falls on the first of a month. When Part B starts depends on when you sign up:
- Sign up in one of the three months before your birthday month: coverage starts on the first day of your birthday month.
- Sign up in your birthday month or the three months after: coverage starts on the first day of the following month.
Working past 65: the 8-month Special Enrollment Period
If you or your spouse are still working and covered by that employer’s group health plan, you can usually delay Part B without a penalty. When the job or the coverage ends, whichever comes first, an 8-month Special Enrollment Period opens. It starts then even if you elect COBRA, and COBRA doesn’t extend it. Retiree coverage, Marketplace plans and other individual insurance never open this window, so people relying on them should sign up during their Initial Enrollment Period.
For drug coverage, you get two full months after the month your employer coverage ends to join a Part D or Medicare Advantage plan, with no penalty if that coverage was creditable. A few timing moves avoid gaps and tax problems:
- Sign up the month before your job coverage ends, so Medicare starts as it stops.
- If you sign up while working, or in the first full month after coverage ends, you can ask to delay your Part B start by up to three months.
- Premium-free Part A backdates up to six months, though never before the month you turned 65, so Medicare advises stopping HSA contributions six months before you apply.
- At an employer with fewer than 20 employees, the job-based plan may not pay unless you have Parts A and B.
If you miss your first window: the General Enrollment Period
Miss your Initial Enrollment Period without qualifying job coverage and your fallback is the General Enrollment Period, January 1 to March 31 each year. Coverage starts the month after you sign up. You may also owe the Part B late penalty: 10% of the standard premium for each full 12-month period you could have had Part B but didn’t, generally for as long as you have Part B. If you have to buy Part A, a late start adds 10% to its premium for twice the number of years you waited.
Medicare also grants exceptional-circumstance Special Enrollment Periods, most lasting six months or more, for situations that arose on or after January 1, 2023. You request them through Social Security, and Part B taken up this way carries no late penalty.
- Losing Medicaid coverage
- A declared disaster or emergency that kept you, or the person helping you, from signing up
- Wrong or misleading information from your employer or health plan
- Release from incarceration, with a window running through the 12th month after release
- Other exceptional conditions, reviewed case by case by Social Security
Yearly windows for changing plans
Once you have Medicare, other windows govern how you get it. Open Enrollment runs October 15 to December 7, with changes effective January 1. During it you can switch between Original Medicare and Medicare Advantage, change Advantage plans, and join, switch or drop a Part D drug plan.
From January 1 to March 31, the Medicare Advantage Open Enrollment Period gives people already in an Advantage plan one switch: to another Advantage plan, or back to Original Medicare with the option of a drug plan. New enrollees who chose Advantage get the same one-time switch in their first three months with Parts A and B.
Special Enrollment Periods for plans follow life events, each on its own clock. A move out of your plan’s service area gives you two full months after the move, starting a month earlier if you tell the plan in advance. People with Medicaid or Extra Help can change drug plans once a month, and the five-star Special Enrollment Period lets you switch once between December 8 and November 30 into a plan rated five stars where one is offered.
The Medigap open enrollment window
Medigap has a one-time window of its own. Medigap Open Enrollment lasts six months, starting the first day of the month you are both 65 or older and enrolled in Part B. During it, insurers can’t refuse to sell you a policy or charge more because of your health. Afterward there is no federal guarantee, although some states give extra rights.
That makes the timing of Part B the timing of Medigap. Delay Part B while on an employer plan and the Medigap window waits until Part B starts. Join Medicare Advantage at 65 and later want Original Medicare with a supplement, and you may pay more or be turned down. The main exception is a trial right: if you joined Advantage when first eligible at 65 and leave within the first 12 months, you return to Original Medicare with special rights to buy a Medigap policy.
Illustrative numbers
Key Medicare dates for someone turning 65 on July 15, 2026
Initial Enrollment PeriodApril 1–October 31, 2026
Premium-free Part A startsJuly 1, 2026
Sign up for Part B in April, May or JunePart B starts July 1, 2026
Sign up for Part B in SeptemberPart B starts October 1, 2026
Medigap Open Enrollment, if Part B starts July 1July 1–December 31, 2026
First Open Enrollment for plan changesOctober 15–December 7, 2026, effective January 1, 2027
If the window is missed with no job-based coverageGeneral Enrollment Period, January 1–March 31, 2027
Signing up in April, May or June leaves no gap in coverage. Waiting past October with no job-based coverage means going without Part B until the General Enrollment Period, and a gap that reaches a full 12 months adds a 10% Part B penalty that generally lasts as long as you have Part B.
At a glance
Medicare enrollment periods at a glance
| Period | When | What you can do | Coverage starts |
|---|---|---|---|
| Initial Enrollment Period | 7 months around your 65th birthday month | Sign up for Parts A and B; join a drug or Advantage plan | Birthday month, or the month after you sign up |
| General Enrollment Period | January 1–March 31 | Sign up for Part B and premium Part A | The month after you sign up |
| Special Enrollment Period for job coverage | Up to 8 months after the job or coverage ends | Sign up for Part B without a penalty | Generally the month after you sign up |
| Open Enrollment | October 15–December 7 | Switch between Original Medicare and Advantage; change plans | January 1 |
| Medicare Advantage Open Enrollment | January 1–March 31 | One switch for Advantage members | The month after the plan gets your request |
| Medigap Open Enrollment | 6 months from when you are 65 or older and in Part B | Buy Medigap without health-based refusal or pricing | When the policy begins |
Put it in your plan
Enrollment periods in MoneyWhatIf
MoneyWhatIf doesn’t model enrollment windows, exact sign-up months or late-enrollment penalties. Its Medicare setting charges premiums from the plan year each person turns 65, and the model ends that person’s marketplace coverage and new HSA contributions at the same age. Employer and retiree coverage aren’t modeled, so if you plan to keep job-based coverage and delay Part B, the projection still charges Medicare premiums from 65. Turn the Medicare setting off only if another spending category already includes those premiums.
Common questions
Enrollment periods FAQs
How do I sign up for Medicare?
Unless you’re enrolled automatically, apply through Social Security: online with a my Social Security account, by calling 1-800-772-1213 or at a local office. Railroad workers contact the Railroad Retirement Board instead. Your card comes in a welcome package about two weeks after you sign up. Drug and Medicare Advantage plans are joined separately, through Medicare.gov’s plan comparison tool, the plan itself or 1-800-MEDICARE.
Can I sign up for Medicare Part B during Open Enrollment?
No. The October 15–December 7 Open Enrollment Period is for changing how you get Medicare, such as switching between Original Medicare and Medicare Advantage or changing drug plans. First-time Part B sign-ups happen in your Initial Enrollment Period, a Special Enrollment Period, or the January 1–March 31 General Enrollment Period.
Does COBRA let me delay Medicare?
No. COBRA isn’t coverage based on current employment, so it doesn’t give you a Special Enrollment Period, and electing it doesn’t extend the 8-month window that starts when your job ends. If you’re 65 or older and leave a job, sign up for Part B within those 8 months even if you keep COBRA; once you have Medicare, COBRA pays after Medicare.
Do I have to re-enroll in Medicare every year?
No. Parts A and B continue as long as you pay any premiums, and your drug or Medicare Advantage plan continues unless you change it or the plan leaves Medicare. Plans can change their premiums, covered drugs and networks each year, so Open Enrollment is the time to compare. If a plan’s contract isn’t renewed, you get a Special Enrollment Period to choose another.