Blog · Medicare
Turning 65 in the Inland Empire: your first-year Medicare checklist
Short answer: your Initial Enrollment Period is 7 months long. It starts 3 months before the month you turn 65 and ends 3 months after it. Sign up before your birthday month and Part B starts the month you turn 65. If you're still covered through current work, you may be able to wait without a penalty. Your one-time Medigap Open Enrollment Period is the 6 months starting when you're 65 or older and enrolled in Part B. Miss your windows and you can face late enrollment penalties that last as long as you have coverage.
Most of the costly Medicare mistakes we see in Colton, San Bernardino, Riverside and Fontana come from timing, not from picking the wrong plan. Someone waits on Part B, drops drug coverage for a few months, or skips Medigap when it was guaranteed. Here's what to do and when.
When can I sign up for Medicare?
Medicare.gov describes your Initial Enrollment Period as 7 months, starting 3 months before you turn 65 and ending 3 months after the month you turn 65. Coverage always starts on the first of a month.
| When you sign up for Part B | When Part B starts |
|---|---|
| Any of the 3 months before the month you turn 65 | The month you turn 65 |
| The month you turn 65, or any of the 3 months after | The next month |
Premium-free Part A starts the month you turn 65. If your birthday falls on the first of the month, coverage starts the month before. Medicare.gov: when coverage starts.
If you already get Social Security benefits (and started at least 4 months before turning 65), you're generally enrolled in Parts A and B automatically, and your Medicare card arrives in the mail. If not, you sign up through Social Security online, by phone at 1-800-772-1213, or at a local office.
What do Part A and Part B cover?
- Part A (hospital insurance): inpatient hospital stays, skilled nursing facility care and hospice. Most people pay no Part A premium.
- Part B (medical insurance): doctor visits, outpatient care, lab work and preventive services, for a monthly premium.
- Part D: drug coverage from private plans, on its own or built into many Medicare Advantage plans.
- Medicare Advantage or Medigap: the two main ways to fill the gaps. You pick one or the other, not both.
I'm still working at 65. Do I need Part B now?
Maybe not. Medicare.gov says if you or your spouse are still working and covered by that job's health plan, you can wait to sign up for Part B until the work or the coverage ends, whichever comes first. You then get an 8-month Special Enrollment Period to sign up without a late penalty. How your employer plan works with Medicare depends on the employer, so ask your benefits administrator before you decide.
Two common traps:
- COBRA doesn't extend your time. Medicare.gov says COBRA coverage doesn't extend your limited time to sign up for Medicare.
- Retiree coverage may require Parts A and B. Coverage from a former job may not pay if you don't have both. Check with the plan before you delay.
If you have a Health Savings Account, Medicare.gov says you and your employer should stop contributions 6 months before you retire or apply for Social Security benefits, to avoid a tax penalty. Medicare.gov: working past 65.
How do Medicare late enrollment penalties work?
Penalties are the costliest timing mistake, because they don't go away. In general terms from Medicare.gov (confirm your own situation before you act):
- Part B: an extra 10% for each full year you could have had Part B but didn't, unless you qualified for a Special Enrollment Period.
- Part D: if you go 63 days or more in a row without Part D or other creditable drug coverage after your Initial Enrollment Period, you can owe an extra 1% of the national base beneficiary premium for each month you went without. That base was $38.99 in 2026. The penalty is added for as long as you have Medicare drug coverage, even if you switch plans.
- Part A: only applies if you have to buy Part A. The premium can go up 10%, for twice the number of years you didn't sign up.
Creditable drug coverage means coverage expected to pay, on average, at least as much as standard Medicare drug coverage. Your employer or plan should tell you in writing whether yours is creditable. Keep that letter.
When should I buy a Medigap policy?
If you plan to stay on Original Medicare, your best time to buy Medigap is your Medigap Open Enrollment Period: the 6 months that start on the first day of the month you're 65 or older and signed up for Part B. Medicare.gov notes that after this period, your options may be limited and a policy may cost more. Medicare.gov: when can I buy Medigap.
If you delay Part B because you're still working, this window doesn't start until you enroll in Part B. So don't sign up for Part B early just to "get it done" if you plan to keep employer coverage for a while. It can start your Medigap clock before you need it.
What is California's Medigap birthday rule?
California gives people who already have a Medicare Supplement policy an extra chance each year. According to the California Department of Insurance, you have 60 days of open enrollment following your birthday each year to switch to another Medigap policy, and the new policy must have the same or lesser benefits than your current one. Your insurer is supposed to remind you of this right before your birthday. California Department of Insurance: Medicare Supplement Insurance.
The birthday rule is a California rule. It doesn't replace your first Medigap Open Enrollment Period, and it doesn't let you move up to richer coverage. Rules can change, so we confirm current requirements before any switch. For free, unbiased counseling, California's SHIP is HICAP at 1-800-434-0222.
Your first-year Medicare checklist
Count from the month you turn 65:
- 6 months before: ask your employer or union whether your coverage continues past 65, and whether your drug coverage is creditable
- 3 months before: your Initial Enrollment Period opens. Sign up for Parts A and B now if you want coverage to start on time
- 2 to 3 months before: list your doctors, medical group, prescriptions and pharmacy, then compare Medicare Advantage, Medigap and Part D options
- Birthday month: Part A and Part B start if you signed up early. Confirm your drug coverage starts with no 63-day gap
- First 6 months with Part B: your Medigap Open Enrollment Period. Buy Medigap now if you're staying on Original Medicare
- 3 months after: your Initial Enrollment Period ends
- October 15 to December 7: Open Enrollment. Review your plan's Annual Notice of Change for next year
Frequently asked questions
How long is the Medicare Initial Enrollment Period?
Seven months. It starts 3 months before the month you turn 65, includes your birthday month, and ends 3 months after it.
Am I enrolled in Medicare automatically at 65?
If you already get Social Security or Railroad Retirement benefits, you're generally enrolled in Parts A and B automatically and your card comes in the mail. If you don't, you need to sign up through Social Security.
Can I delay Part B if I have insurance through work?
Often yes, if the coverage is from current employment for you or your spouse. When the job or coverage ends, you get an 8-month Special Enrollment Period. COBRA and retiree coverage don't count the same way, so check before you delay.
What is the Medigap Open Enrollment Period?
It's a one-time 6-month window that starts the first day of the month you're 65 or older and enrolled in Part B. After it ends, your Medigap options may be limited and a policy may cost more.
How does the California birthday rule work?
If you already have a Medicare Supplement policy in California, the Department of Insurance says you have 60 days following your birthday each year to switch to a policy with the same or lesser benefits. We confirm the current rules before any switch.
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