Retiring Soon? Don’t Overlook Medicare Enrollment Deadlines and Costs

Retirement planning usually starts with questions about savings, investments, Social Security, pensions, and income. But there is another major piece that deserves attention before you retire:

Healthcare.

For many people approaching retirement, Medicare becomes one of the most important planning topics around age 65. The timing of enrollment, the type of coverage you choose, drug coverage decisions, and your expected out-of-pocket costs can all affect your retirement income plan.

Medicare decisions are especially important because some deadlines are time-sensitive, and missing them may lead to late enrollment penalties or gaps in coverage. Medicare explains that the Initial Enrollment Period generally lasts seven months, starting three months before the month you turn 65 and ending three months after the month you turn 65. [medicare.gov]

At Landmark Financial, we do not replace Medicare.gov, Social Security, or a Medicare insurance specialist. But Medicare decisions are still part of a broader retirement planning conversation. Your healthcare costs, enrollment timing, premiums, and coverage choices can all influence how much income you may need in retirement.

If retirement is within the next few years, now is the time to understand how Medicare fits into the bigger picture.

What Medicare decisions should you review before retiring?

Before retiring, you should review:

1. When your Medicare Initial Enrollment Period begins
2. Whether you should enroll at age 65 or delay due to employer coverage
3. Medicare Part A, Part B, and Part D costs
4. Whether your prescription drug coverage is creditable
5. Potential late enrollment penalties
6. Medicare Advantage, Original Medicare, and Medigap options
7. How Medicare premiums fit into your retirement income plan
8. How healthcare costs may affect taxes, cash flow, and withdrawal strategy

A Medicare decision should not be reviewed in isolation. It should be part of your full retirement income plan.

Why Medicare planning matters before retirement

Healthcare costs can be one of the largest and most unpredictable expenses in retirement.

Medicare can help cover many healthcare costs, but it does not cover everything. Premiums, deductibles, coinsurance, prescriptions, dental, vision, hearing, long-term care, and supplemental coverage may all need to be planned for separately depending on the coverage you choose.

In 2026, the standard Medicare Part B premium is $202.90 per month, and the Part B annual deductible is $283, according to CMS. [cms.gov], [medicare.gov]

Medicare Part A covers inpatient hospital, skilled nursing facility, hospice, inpatient rehabilitation, and some home health care services, and CMS notes that about 99% of Medicare beneficiaries do not pay a Part A premium because they have at least 40 quarters of Medicare-covered employment. [cms.gov]

That said, “premium-free” does not mean “cost-free.” In 2026, the Medicare Part A inpatient hospital deductible is $1,736 per benefit period, and cost-sharing may apply for longer hospital or skilled nursing stays. [cms.gov], [medicare.gov]

For retirement planning, the key question is not simply, “Will I have Medicare?”
A better question is: “How will Medicare costs fit into my monthly retirement income plan?”

Understand your Medicare enrollment window

Your first Medicare enrollment window is called the Initial Enrollment Period.

Medicare states that this period generally lasts seven months. It begins three months before the month you turn 65, includes your birthday month, and ends three months after that month. [medicare.gov]

If you miss this window and do not qualify for a Special Enrollment Period, you may have to wait to enroll and may pay a late enrollment penalty. Medicare explains that missed enrollment can result in monthly late enrollment penalties that are usually charged for as long as you have that type of coverage. [medicare.gov], [medicare.gov]

This is why Medicare planning should not wait until the month you retire.

If you are approaching age 65, or if you are already 65 and still working, you should know which enrollment rules apply to your situation.

Be careful if you plan to work past 65

More people are choosing to work beyond age 65. If that applies to you, Medicare timing may work differently.

Medicare.gov explains that if you or your spouse are still working and have health insurance from current employment, you may be able to wait to sign up for Medicare without paying a late enrollment penalty. [medicare.gov]

However, not all coverage works the same way. Medicare advises people with employer coverage to ask the employer that provides health insurance whether they need to sign up for Part A and Part B when they turn 65. Medicare also warns that if you do not sign up for Part A and Part B when required, job-based coverage might not cover the costs for services you receive. [medicare.gov]

If you delay Medicare because you have active employer group health coverage, you may qualify for an eight-month Special Enrollment Period after employment or employer coverage ends. Social Security states that if you were covered by an active employer group health plan since turning 65 and that coverage ended within the last eight months, you can enroll in Part B without penalty. [ssa.gov], [medicare.gov]

This is one of the most important Medicare timing issues for pre-retirees.

Before retiring, ask your employer or benefits administrator:

• Is my current coverage considered employer group health plan coverage?
• Is my prescription drug coverage creditable?
• When does my employer coverage end?
• Do I need Medicare Part A, Part B, or Part D at age 65?
• What paperwork do I need when I retire?

CMS provides Form CMS-L564, Request for Employment Information, which is used as proof of group health plan coverage based on current employment when applying for Medicare during a Special Enrollment Period. [cms.gov]

Do not overlook Medicare late enrollment penalties

Late enrollment penalties can be frustrating because they may last for a long time.

Medicare states that late enrollment penalties are added to your monthly premium, are not a one-time fee, and are usually charged for as long as you have that type of coverage. [medicare.gov]

For Medicare Part B, Medicare says you generally pay an extra 10% for each year you could have signed up for Part B but did not, unless you qualify for a Special Enrollment Period or another exception. [medicare.gov], [medicare.gov]

For Medicare Part D, Medicare states that the late enrollment penalty may be added permanently to your Medicare drug coverage premium if you go without Part D or creditable prescription drug coverage for 63 or more days in a row after your Initial Enrollment Period ends. [medicare.gov], [cms.gov]

This matters because penalties can affect your retirement cash flow year after year.

The planning takeaway is simple: do not assume you can “figure it out later.” Medicare enrollment timing deserves attention before you leave employer coverage or reach age 65.

Review prescription drug coverage before you retire

Prescription drug coverage is another area where timing matters.

If you have employer or union prescription drug coverage, you need to know whether it is considered creditable coverage. CMS explains that creditable prescription drug coverage is coverage expected to pay, on average, at least as much as Medicare’s standard prescription drug coverage. [cms.gov]

Medicare’s Part D late enrollment penalty may apply if you go 63 or more days without Part D or other creditable prescription drug coverage after your Medicare Initial Enrollment Period ends. [medicare.gov], [cms.gov]

Before retiring, ask:

• Is my current prescription drug coverage creditable?
• Will I lose employer drug coverage when I retire?
• Do I need a standalone Part D plan?
• If I choose Medicare Advantage, does it include prescription drug coverage?
• What medications do I take now, and how might coverage change?

This is also a good time to gather your medication list and compare expected costs under different coverage options with a Medicare specialist or Medicare.gov resources.

Understand the difference between Medicare enrollment and Medicare Open Enrollment

Medicare Open Enrollment is not the same as your first chance to sign up for Medicare.

Medicare Open Enrollment happens each year from October 15 through December 7, and it is the period when people who already have Medicare can make certain changes to their coverage for the following year. Medicare.gov states that changes made during Open Enrollment are effective January 1 of the next year. [medicare.gov]

During Open Enrollment, you may be able to change Medicare Advantage Plans, switch drug plans, join or drop certain coverage, or switch between Original Medicare and Medicare Advantage depending on your current coverage. [medicare.gov]

But Open Enrollment is not a substitute for your Initial Enrollment Period for Part A and Part B.

If you are turning 65 or leaving employer coverage, make sure you understand which enrollment window applies to you.

Medicare costs can affect your retirement income plan

Medicare costs should be built into your retirement budget.

In 2026, CMS reported the standard Medicare Part B premium is $202.90 per month, and the Part B deductible is $283. [cms.gov], [medicare.gov]

CMS also reported the Medicare Part A inpatient hospital deductible is $1,736 per benefit period in 2026, with additional daily coinsurance amounts for longer hospital or skilled nursing facility stays. [cms.gov], [medicare.gov]

Your actual healthcare costs may also include:

• Medicare Part B premiums
• Medicare Part D premiums
• Medicare Advantage premiums, if applicable
• Medigap premiums, if applicable
• deductibles
• copays and coinsurance
• prescriptions
• dental, vision, and hearing expenses
• long-term care expenses
• income-related premium adjustments, if applicable

CMS notes that some beneficiaries with higher income pay an income-related monthly adjustment amount in addition to the standard Part B premium. [federalregister.gov], [medicare.gov]

This is where Medicare connects directly to financial planning.

Your healthcare costs may affect:

• how much monthly income you need
• when you claim Social Security
• how much you withdraw from retirement accounts
• whether Roth conversions make sense
• how much cash you keep available
• how you prepare for unexpected medical expenses

A Medicare decision is not just a healthcare decision. It is part of your retirement income plan.

Medicare choices should be coordinated with Social Security

Medicare and Social Security often show up around the same season of life, but they do not follow the exact same timeline.

Many people become eligible for Medicare at age 65, while Social Security retirement benefits can begin as early as age 62, with reduced benefits before full retirement age. The Social Security Administration states that if you delay Social Security beyond full retirement age, your benefit can increase up to age 70. [kff.org]

This creates planning decisions.

For example:

• If you retire before age 65, how will you handle healthcare before Medicare?
• If you delay Social Security but enroll in Medicare, how will you pay Medicare premiums?
• If you keep working past 65, should you enroll in Medicare or stay on employer coverage?
• If your income is higher before retirement, could that affect Medicare premium adjustments later?

These moving parts should be reviewed together.

What to review 12 to 24 months before retirement

If retirement is within the next year or two, do not wait until the last minute to review Medicare.

Here is a practical checklist:

24 to 12 months before retirement

• Estimate your retirement date
• Review whether you will retire before, at, or after age 65
• Ask your employer how coverage works after 65
• Confirm whether prescription drug coverage is creditable
• Estimate Medicare premiums and out-of-pocket costs
• Review Social Security claiming options
• Build healthcare costs into your retirement income plan

12 to 6 months before retirement

• Identify your Medicare Initial Enrollment Period or Special Enrollment Period
• Gather employer coverage documentation if working past 65
• Review Part A, Part B, Part D, Medicare Advantage, and Medigap considerations
• Compare expected prescription costs
• Review how Medicare premiums will be paid
• Coordinate coverage timing to avoid gaps

3 months before retirement or age 65

• Confirm enrollment deadlines
• Submit required applications or forms
• Review first-month coverage dates
• Review premium costs and automatic payments
• Confirm that employer coverage and Medicare timing align

The goal is to avoid rushed decisions when retirement is already busy.

A local planning note for Arkansas and Arizona retirees

Retirement planning is personal, but local realities matter.

A retiree in Fort Smith, Rogers, Jonesboro, Little Rock, Conway, or Russellville may be coordinating Medicare decisions with Social Security, pension income, retirement account withdrawals, or a business transition.

A retiree in Scottsdale or Surprise may be thinking about Medicare costs, healthcare access, taxes, housing costs, and retirement income timing.

Landmark Financial serves clients across Arkansas and Arizona, as well as nationwide. While Medicare enrollment decisions should be confirmed through Medicare.gov, Social Security, or a Medicare insurance specialist, our team can help clients understand how healthcare costs fit into a broader retirement income plan.

Final thoughts

If you are retiring soon, Medicare deserves a place in the retirement conversation.

The deadlines matter. The costs matter. The penalties matter. And the decisions you make may affect your monthly cash flow for years to come.

Before you retire, take time to review:

• when you need to enroll
• whether you can delay because of employer coverage
• how prescription drug coverage works
• what penalties may apply
• what premiums and out-of-pocket costs may look like
• how Medicare fits with Social Security, taxes, and retirement income

Retirement should begin with clarity, not confusion.

Healthcare is too important to leave until the last minute.