Guide to Medicare Enrollment: When to Enroll and Coverage Options
- Kathleen Bennett
- Aug 25
- 4 min read
Updated: Sep 6
Confused about how to enroll in Medicare?
This guide will help you understand when to sign up and important rules you need to know. We answer these frequently asked questions about Medicare enrollment:
It’s always best to get individualized assistance for your medical needs. Get in touch with a local Oregon Medicare agent near you.
When can I enroll in Medicare?
Options for Medicare Enrollment
There are three times you can enroll:
The Medicare Initial Enrollment Period (IEP) when you first turn 65.
The General Enrollment Period between January 1-March 31 each year.
The Medicare Special Enrollment Period (SEP) which is only available if you have a qualifying life event.
The Medicare Initial Enrollment Period (IEP)
The Medicare Initial Enrollment Period (IEP) starts 3 months before your 65th birthday and ends 3 months after your birthday. This is the best and most cost-effective time to enroll in Medicare. You can use Medicare.gov’s Estimator to learn when you will become eligible for Medicare.
During this time, you should:
Sign up to receive Social Security benefits, if you haven’t already.
Receive your Medicare card in the mail.
Consider enrolling in Part B and Part D.
Coverage will start the month you turn 65 if you sign up in the 3 months before your birthday. If you wait until the month you turn 65 or during the 3 months after, coverage will begin the next month.
The General Enrollment Period
After your 65th birthday, you may enroll in Medicare between January 1-March 31 each year during the General Enrollment Period. However, you may pay a monthly late enrollment penalty if you don’t qualify for a Special Enrollment Period. This is why it is always best to enroll when you first become eligible for Medicare, typically when you turn 65.
The Medicare Special Enrollment Period (SEP)
You may be able to enroll or change your plan during a Medicare Special Enrollment Period (SEP) if you have qualifying life event such as:
Losing or gaining other health coverage, like an employer-sponsored health coverage or Medicaid
Moving to an address outside of your current plan’s service area
Family status changes, like getting married or adopting a child
The deadlines for SEPs depend on the qualifying event. Learn more about SEPs on Medicare.gov’s site or contact your local agent for support.
Oregon Medicare enrollment deadlines are the same as the rest of the country. There are no enrollment periods specific to Oregon.
When will my Medicare coverage start?
Your Medicare coverage will start depending on when you enroll.
If you enrolled during the Initial Enrollment Period, coverage will start the month you turn 65 if you sign up in the 3 months before your birthday. If you wait until the month you turn 65 or during the 3 months after, coverage will begin the next month.
If you enrolled during the General Enrollment Period, coverage will start the month after you sign up.
If you enrolled during a Special Enrollment Period, the start date will vary, but will typically be the month after you sign up.
How do I choose my Medicare coverage?
Creating your Medicare plan depends on your medical needs and budget. Here is a quick summary of the primary Medicare parts. We recommend speaking with a local Medicare agent to get guidance on which parts you may need.
Part A (Hospital): Part A covers inpatient care in hospitals, skilled nursing facility care, hospice care, and home health care. If you or your spouse contributed to Medicare taxes for a certain time, you can get Plan A for no cost.
Part B (Medical): Part B helps cover medically necessary doctor’s services, outpatient care, home health services, durable medical equipment, mental health services, limited outpatient prescription drugs, and other medical services. Part B also covers many, but not all preventive services.
Part C (Medicare Advantage): Medicare Advantage is a Medicare-approved plan from a private company that bundles Parts A, B and sometimes D. A Medicare Advantage Plan will likely require you to use doctors in the plan’s network. This can be challenging for rural patients.
Part D (Prescriptions): Part D, sometimes called a “Prescription Drug Plan” (PDP), helps pay for your prescription drugs, including many recommended shots or vaccines. Your drug costs will vary based on the plan you choose.
Do I need Medicare Part B when I first enroll?
Yes, it is recommended to enroll in Medicare Part B when you first become eligible. Part B premiums will increase about 10% for each 12-month period that you could have enrolled but did not, unless you qualify for a Special Enrollment Period.
Explore the advantages of Medicare Part B and enrollment considerations for more details.
Do I need Medicare Part D when I first enroll?
You will likely need to enroll in a Medicare Prescription Drug Plan (Part D) as prescriptions are not automatically covered under Medicare Parts A or B. Like Medicare Part B, if you delay, you will have increased premiums due to the late enrollment penalty.
Should I get Medicare supplemental plans when I first enroll?
Yes! When you first become eligible for Medicare is the best time to purchase a Medicare supplement policy because insurance companies cannot deny you based on pre-existing conditions. This broadens your choices for insurance companies and therefore, providers and premiums.
If you are continuing to work past 65, you may qualify for a Special Enrollment Period that will allow you this same benefit when you decide to stop working and lose employer-provided coverage.
Who can help me enroll in Medicare and manage my plan?
You can get free Medicare enrollment assistance through your State Health Insurance Assistance Program (SHIP) or an independent, licensed broker who works with multiple insurance companies. Hillock Insurance is a licensed broker serving Medicare patients in northeastern Oregon including Wallowa, Union, and Baker counties.
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