Medicare can feel straightforward from a distance: turn 65, enroll, pick a plan, and move on. In reality, there are multiple enrollment periods, several different parts of Medicare, important differences between Original Medicare and Medicare Advantage, and health and drug plans that can change from year to year.
That makes the months leading into Medicare Open Enrollment an important time to understand what you currently have and whether it still fits your needs. For 2027 coverage, Medicare beneficiaries can begin comparing available health and drug plans on October 1, 2026, while the annual Open Enrollment Period runs from October 15 through December 7, 2026. Changes made during that period generally take effect January 1, 2027 (Medicare).
Turning 65? Know Your Initial Enrollment Window
For most people, Medicare eligibility begins around age 65, and the Initial Enrollment Period lasts seven months. It begins three months before the month you turn 65, includes your birthday month, and continues for three months afterward (Medicare).
The exact date your coverage begins depends on when you enroll. If you sign up before the month you turn 65, coverage generally begins during your birthday month; enrolling later in the seven-month window may result in coverage beginning the following month (Medicare).
Employer-sponsored insurance can also affect when it makes sense to enroll. Some people covered through their own or a spouse’s current employment may qualify for a Special Enrollment Period, which is one reason Medicare timing should be evaluated based on your individual situation rather than simply assuming everyone must make the same decision at 65 (Medicare).
Understanding Medicare Parts A and B
Medicare Part A is commonly referred to as hospital insurance. It helps cover inpatient hospital care, skilled nursing facility care, hospice care, and certain home health services. Most people do not pay a monthly Part A premium because they or their spouse paid Medicare taxes long enough while working, generally at least 10 years (Medicare; Medicare).
It is important to distinguish skilled nursing coverage from ongoing custodial long-term care. Medicare Part A can cover qualifying skilled nursing facility care, but Medicare generally is not designed to cover indefinite custodial long-term care.
Part B is medical insurance and generally covers services such as doctor visits, outpatient care, durable medical equipment, many preventive services, and other medically necessary care (Medicare).
Together, Parts A and B make up Original Medicare and form the foundation for the other coverage decisions that come next.
Medicare Advantage vs. Original Medicare With a Supplement
Once Parts A and B are in place, one of the larger decisions is how you want to receive your coverage. With Original Medicare, the federal government administers Part A and Part B coverage. You can generally see any doctor or hospital in the United States that accepts Medicare, and you may choose to add separate Part D prescription coverage and a Medicare Supplement Insurance policy, commonly called Medigap, to help cover certain out-of-pocket costs (Medicare).
A Medicare Advantage plan, or Part C, is offered through a Medicare-approved private insurance company and provides an alternative way to receive Part A and Part B benefits. Most Medicare Advantage plans also include Part D drug coverage, and some offer additional benefits such as dental, vision, or hearing coverage. Depending on the plan, networks, referrals, prior authorization requirements, copays, deductibles, and other rules may apply (Medicare).
Neither approach is automatically right for everyone. Your doctors, prescriptions, travel habits, budget, preferred hospital systems, risk tolerance, and location can all affect which structure is more appropriate.
What Does a Medicare Supplement Do?
Medicare Supplement Insurance, or Medigap, works alongside Original Medicare rather than replacing it. These private insurance policies can help pay certain costs that Original Medicare leaves to the beneficiary, including copayments, coinsurance, and in some cases deductibles. Medigap generally does not include prescription drug coverage, so someone using Original Medicare may also choose a separate Part D drug plan (Medicare).
Medigap also has its own enrollment rules. Your one-time Medigap Open Enrollment Period generally begins the first month you have Part B and are age 65 or older, and during that six-month period an insurer cannot deny you a Medigap policy because of pre-existing health problems (Medicare).
That is different from the annual October 15 through December 7 Medicare Open Enrollment Period and is one reason the terminology can become confusing.
Part D: Why Prescription Coverage Deserves an Annual Review
An easy way to remember Medicare Part D is simply D for drugs. Part D helps cover prescription medications and can be obtained either through a stand-alone Medicare drug plan for people with Original Medicare or through many Medicare Advantage plans that include prescription coverage (Medicare).
The important point is that Part D plans are not all identical. Costs and the specific prescriptions covered can vary by plan, and those details can change over time.
Medicare recommends reviewing the Evidence of Coverage and Annual Notice of Change that plans send each year. Those documents outline changes to costs, coverage, provider networks, service areas, and other plan details that take effect the following January (Medicare). That means even someone who has been happy with the same drug plan for years should still review it before simply allowing it to renew.
Why October 1 Matters
Beginning October 1, 2026, Medicare beneficiaries can start comparing their current health or drug coverage with available options for 2027. Open Enrollment itself then begins October 15 and ends December 7 (Medicare). That gives you roughly two weeks to review your current plan, gather your prescription list and doctor information, compare available options, and ask questions before the window for making changes officially opens.
Even if your existing plan is still offered for 2027, that does not necessarily mean everything about it remains the same. Premiums, copays, formularies, provider networks, and other plan details may change from one year to the next.
What to Bring to a Medicare Review
A productive Medicare review begins with understanding your personal situation. Consider bringing:
- Your current Medicare or health insurance information
- A complete list of prescription medications
- Your preferred doctors and specialists
- Your preferred hospitals or health systems
- Questions or concerns about your existing coverage
- Information about any anticipated changes to your healthcare needs
At Wealth Financial Services & Tax Advisory, our Medicare team uses that information to review the available options and help explain how different plans may fit your individual circumstances.
That process is useful when you are enrolling in Medicare for the first time, but it can be just as valuable during an annual review. Prescriptions change, doctors change, health needs change, and plans change.
Medicare Planning Does Not Stop After Open Enrollment
Open Enrollment gets most of the attention, but questions can arise throughout the year. Our Medicare agents are available year-round to help clients with Medicare questions, coverage concerns, claims issues, and other situations that may come up. There is no charge for a Medicare consultation with our team.
The goal is not simply to pick a plan every October. It is to make sure you understand your coverage and have a resource available when questions arise. If you would like to review your Medicare coverage before Open Enrollment, call 847-499-3454 today to connect with our Medicare team!
To hear more on this topic, watch the full video here!
