Your Pre-December Medicare Checklist: What to Review Before Enrollment Closes

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By Harley Gill

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Your Pre-December Medicare Checklist: What to Review Before Enrollment Closes
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The Medicare plan that worked well in 2026 may not offer the same protection in 2027. Premiums can change, prescription costs may rise, and familiar doctors could leave a plan’s network.

The good news is that reviewing your coverage does not mean you must switch plans.

This Medicare open enrollment checklist explains what to examine before December 7, how the 2027 changes affect your budget, and which questions deserve attention before making a final decision.

1. Mark December 7 on Your Calendar

December 7
Source: Canva

The most important date on the Medicare calendar is December 7, 2026. This is the final day of the annual Open Enrollment Period for most changes to Medicare Advantage and Medicare Part D coverage for 2027.

The enrollment period began October 15, and changes made during this window generally take effect January 1, 2027. If you are satisfied with your existing coverage and the plan continues, you may not need to make any changes.

However, doing nothing is different from making an informed decision to stay. Your existing plan can change its costs, benefits, and provider network even when you remain enrolled.

Important DateEnrollment EventWhat It Means
October 15, 2026Open enrollment beginsCompare and change eligible plans
December 7, 2026Annual enrollment closesDeadline for most 2027 plan changes
January 1, 2027New coverage beginsSelected changes take effect
January 1 to March 31, 2027Medicare Advantage enrollment windowEligible Advantage members can make one change
December 8, 2026 to February 28, 2027Special window for certain plan nonrenewalsAdditional options for affected members

These dates matter because different enrollment periods serve different purposes. The January through March window is not a general extension for everyone who missed December 7.

People turning 65, losing qualifying employer coverage, or experiencing certain other events may have separate enrollment rights. Those deadlines depend on individual circumstances rather than the annual December cutoff.

2. Read Your Annual Notice of Change Before Anything Else

Notice
Source: Canva

Every fall, Medicare Advantage and Part D plans send members an Annual Notice of Change, commonly called the ANOC. This document explains how the plan’s costs and coverage will change in the coming year.

It is one of the most useful documents to review before choosing your 2027 coverage. A plan that looks unchanged on the surface may have adjusted its deductible, drug coverage, copayments, or provider network.

Pay particular attention to the monthly premium, annual deductible, specialist visit charges, hospital costs, and prescription coverage. Review the Evidence of Coverage document as well, since it provides more detailed information about benefits and restrictions.

What If Your Current Plan Is Ending?

This question is especially important for the 2027 enrollment season. An October 2026 KFF analysis found that approximately 4.3 million Medicare beneficiaries were enrolled in Medicare Advantage or stand-alone prescription drug plans scheduled to terminate at the end of 2026.

That does not mean 4.3 million people are losing Medicare itself. It means their existing private plans are ending, so they need to understand what replacement coverage or enrollment options will be available.

If you receive a notice that your plan is terminating or will not be renewed, read it immediately. Certain plan nonrenewals create a special enrollment opportunity beyond December 7, but you should confirm your exact rights and avoid assuming you will automatically receive an equivalent plan.

3. Review Every Prescription You Take

Prescription
Source: Canva

Prescription drug coverage deserves close attention because the cheapest monthly premium does not always produce the lowest annual cost. A plan can charge less each month while requiring substantially more money at the pharmacy.

Start by making a complete list of your medications, including brand names, generic alternatives, dosages, and how frequently prescriptions are filled. Then check each medication against the plan’s 2027 formulary, which is its official list of covered drugs.

Pay attention to whether your medications have moved into different pricing tiers. A change from a preferred generic to a more expensive tier can increase your expenses even if the medication remains covered.

Important Medicare Drug Changes for 2027

Medicare’s prescription drug benefit includes important financial protections, but several amounts are changing for 2027. Understanding those changes helps prevent confusion when comparing plans.

Part D Feature20262027
Annual out-of-pocket threshold$2,100$2,400
Maximum annual deductible$615$700
Cost sharing after reaching the threshold$0 for covered Part D drugs$0 for covered Part D drugs
Medicare negotiated drug pricesFirst 10 drugs effective15 additional drugs effective

The $2,400 threshold for 2027 is especially important for people taking expensive prescriptions. Once qualifying out-of-pocket spending reaches the threshold, covered Part D drugs generally have no further cost sharing for the rest of the calendar year.

However, the threshold does not mean every medication expense is capped at $2,400. Monthly premiums, drugs outside Part D coverage, and certain payments made outside the plan do not necessarily count toward that protection.

Check Whether Your Medications Have Restrictions

A medication appearing on the formulary does not always mean it can be obtained without additional conditions. Some plans require prior authorization, which means the plan must approve coverage before paying for the prescription.

Others use step therapy, requiring a patient to try another covered medication first, or quantity limits that restrict how much can be dispensed. These rules can affect how easily you receive treatment and what you pay.

Review these requirements before choosing a plan, especially if you take medications for chronic conditions. Your doctor or pharmacist may also help explain whether a covered alternative would be medically appropriate.

4. Compare Your Pharmacy Options

Pharmacy
Source: Canva

Your preferred pharmacy can affect what you pay under Medicare Part D. Plans may have preferred pharmacies offering lower cost sharing and standard network pharmacies charging more for the same prescription.

For example, a hypothetical medication might cost $12 per month at a preferred pharmacy and $28 at another participating pharmacy. That difference adds up to $192 over a year for just one medication.

People taking several prescriptions could see a much larger difference. A familiar pharmacy may still participate in a plan but lose its preferred status for 2027.

Check the pharmacies near your home, especially if transportation is difficult or you have mobility limitations. If you spend part of the year in another state, also consider whether your plan offers convenient pharmacy access in both locations.

Mail-order pharmacy services may offer additional convenience or savings for some medications. Compare the actual costs and delivery arrangements rather than assuming mail order is always cheaper.

5. Calculate the Real Annual Cost, Not Just the Premium

One of the most common Medicare shopping mistakes is comparing plans only by their monthly premiums. A $10 plan may look more attractive than a $40 plan, but its deductible and prescription costs could make it more expensive overall.

The more useful question is how much you are likely to spend over an entire year. That includes monthly premiums, prescription copayments, deductibles, and other covered expenses that apply to your situation.

Consider this hypothetical comparison of three stand-alone Part D plans for someone taking several regular medications.

Hypothetical PlanMonthly PremiumEstimated Annual Drug CostsCombined Annual Cost
Plan A$12$840$984
Plan B$42$360$864
Plan C$5$1,150$1,210

In this example, Plan B has the highest monthly premium but the lowest projected annual total. Choosing Plan B instead of Plan C would save $346 over the year under these assumptions.

These are illustrative figures, not actual 2027 plan quotes. The comparison includes plan premiums and estimated out-of-pocket expenses for covered prescriptions, but excludes Part B premiums and any noncovered medications.

The lesson is that a low premium is only one part of a much larger calculation. A plan’s total estimated annual cost is usually a more useful starting point for comparing drug coverage.

6. Confirm Your Doctors and Hospitals Are Still Covered

Doctors
Source: Canva

For people enrolled in Medicare Advantage, the provider network can be just as important as the monthly premium. A plan with attractive benefits may become less practical if trusted doctors or nearby hospitals are no longer in its network.

Start with your primary care doctor and any specialists you see regularly. Include cardiologists, oncologists, endocrinologists, physical therapists, and other providers involved in ongoing treatment.

Next, review the hospitals, imaging centers, outpatient facilities, and rehabilitation providers you might need. Some plans have separate arrangements for hospitals and medical groups, so checking only the doctor’s name may not provide the full picture.

Ask About the Specific 2027 Plan

A medical office accepting an insurance company’s plans does not necessarily mean it accepts every Medicare Advantage product offered by that company. Confirm participation in the exact plan you are considering for 2027.

Network directories can change, and provider information is not always updated immediately. Contact the plan and the doctor’s office when a provider’s continued participation is essential to your decision.

For people with complex conditions, continuity of care can be particularly valuable. Changing plans solely to save a small premium may not be worthwhile if it creates expensive or inconvenient changes in medical care.

7. Understand the Two Different Out-of-Pocket Limits

Understand the Two Different Out-of-Pocket Limits
Source: Canva

Medicare uses different rules for prescription drug spending and medical service spending. Confusing the two can lead to a false impression of how much protection a plan provides.

The 2027 Part D threshold of $2,400 concerns qualifying expenses for covered prescription drugs. Medicare Advantage plans have a separate annual out-of-pocket limit for covered Part A and Part B medical services.

Suppose a hypothetical Medicare Advantage plan has a $6,000 in-network medical out-of-pocket maximum. That maximum does not mean all your healthcare expenses, including premiums and prescriptions, are limited to $6,000.

You could still owe Part B premiums, any additional plan premiums, and qualifying prescription drug expenses under separate rules. Noncovered services may also create expenses outside those limits.

Check Hospital and Specialist Charges

Review what you would pay for hospital admissions, outpatient surgery, emergency visits, and specialist appointments. These expenses may become more important than routine primary care copayments if you experience a serious illness.

Compare the plan’s annual medical out-of-pocket maximum with the amount your retirement budget could reasonably absorb. A low monthly premium may come with greater financial exposure when extensive treatment is needed.

Original Medicare works differently because it generally does not have an annual out-of-pocket maximum for covered Part A and Part B services. Supplemental coverage such as Medigap can help reduce certain costs, but its availability and premium must be considered separately.

8. Reconsider Original Medicare Versus Medicare Advantage

Medicare
Source: Canva

Annual enrollment is an opportunity to review how you receive Medicare coverage, not simply which private plan has the lowest advertised price. Original Medicare and Medicare Advantage provide different approaches to managing medical bills and provider access.

Original Medicare includes Part A for hospital insurance and Part B for medical insurance. People can add a stand-alone Part D plan for prescriptions and may purchase Medigap to help cover certain out-of-pocket costs.

Medicare Advantage, also called Part C, provides Part A and Part B benefits through a Medicare-approved private plan. Most plans include prescription drug coverage, and many offer extra benefits such as dental, vision, or hearing services.

Important FeatureOriginal MedicareMedicare Advantage
Doctor accessAny provider accepting MedicareOften plan networks
Drug coverageUsually separate Part D planIncluded in most plans
Medical out-of-pocket limitNo general annual maximumAnnual plan limit
Supplemental coverageMedigap may be availableMedigap cannot supplement it
Extra benefitsUsually limitedOften includes additional benefits

Neither option is automatically better for every retiree. The right comparison depends on medical needs, provider preferences, financial resources, travel habits, and available plans.

Someone who wants broad access to doctors across the country may value Original Medicare. Another person may prefer the coordinated network and additional benefits of a Medicare Advantage plan.

The important step is to compare actual coverage, likely expenses, and possible financial risks. Advertising should not replace a detailed review of plan documents.

9. Be Careful About Switching Away From Medicare Advantage

One of the most easily overlooked Medicare rules concerns supplemental insurance. Switching from Medicare Advantage to Original Medicare does not automatically guarantee that you can buy a Medigap policy.

Under federal rules, most people have a six-month Medigap Open Enrollment Period beginning when they are 65 or older and first enrolled in Part B. During this period, insurers generally cannot deny coverage based on existing health conditions.

After that window closes, purchasing Medigap may be more difficult in many states. Insurers may use medical underwriting unless you qualify for a guaranteed issue right or a separate state protection.

Why This Matters Financially

Consider a hypothetical retiree who leaves Medicare Advantage expecting to purchase Medigap Plan G. If an insurer can legally deny the application or charge a substantially higher premium, the retiree’s financial situation may look very different from what was expected.

Original Medicare without supplemental protection can leave beneficiaries responsible for significant coinsurance and deductible expenses. The decision should therefore consider Medigap eligibility before the Medicare Advantage switch takes effect.

Certain circumstances, including some plan terminations or trial rights, provide additional Medigap protections. Because these rights depend on specific facts and sometimes state law, confirm eligibility with a State Health Insurance Assistance Program or state insurance department.

10. Review Additional Benefits Without Letting Them Decide Everything

Dental
Source: Canva

Dental, vision, hearing, transportation, and other supplemental benefits can make Medicare Advantage plans attractive. However, the value of these benefits depends on what is actually covered and whether you are eligible to use them.

For example, a plan might advertise a generous dental allowance while limiting which services qualify or requiring participating dentists. Some benefits also have frequency limits, annual maximums, or other conditions.

Review the benefit details before assigning them a dollar value in your comparison. An allowance is not necessarily equivalent to cash that can be spent freely.

The same principle applies to benefits for groceries, transportation, and support services. Some are available only to members meeting specific medical or eligibility requirements.

Medical coverage should remain central to the decision. Extra benefits are useful when they meet a real need, but they should not distract from substantial differences in hospital costs, prescription coverage, or doctor access.

11. Check Whether You Qualify for Help Paying Medicare Costs

Many retirees focus on finding cheaper insurance without first checking whether they qualify for assistance. Federal and state programs may help eligible people pay premiums, deductibles, and prescription expenses.

One important program is Extra Help, which assists people with limited income and resources with Medicare Part D costs. Eligibility depends on financial circumstances, and some beneficiaries qualify automatically through other assistance programs.

Medicare Savings Programs are another important option. Depending on the program and state eligibility rules, they may cover Part B premiums and sometimes other Medicare costs.

Do Not Assume Your Income Is Too High

Financial assistance rules can change, and some states use more generous eligibility standards than the basic federal guidelines. A retiree who did not qualify previously may become eligible after a reduction in income or assets.

For someone living on a fixed retirement budget, assistance with the Part B premium could make a meaningful difference. Medicare’s standard Part B premium was $202.90 per month in 2026, which equals $2,434.80 over 12 months.

The 2027 premium should be checked once the official amount is available, rather than assuming the 2026 figure will remain unchanged. Anyone with limited income should also ask about state assistance before choosing a plan solely on the basis of its premium.

12. Look for Medicare Premium Surcharges

Medicare Premium Surcharges
Source: Canva

Some retirees pay higher Part B and Part D premiums because their income exceeds certain thresholds. This additional charge is called the Income-Related Monthly Adjustment Amount, or IRMAA.

Medicare generally uses income information from the tax return filed two years earlier to determine whether a surcharge applies. For 2027 premiums, that generally means income reported on a 2025 tax return.

This can create an unexpected situation for someone who recently retired. Their income may have fallen substantially, but Medicare could initially calculate a surcharge using the higher earnings reported during their working years.

When a Surcharge Can Be Reduced

Social Security allows beneficiaries to request an IRMAA adjustment after qualifying life-changing events. Examples include retirement, a reduction in work hours, divorce, or the death of a spouse.

A qualifying event does not automatically eliminate the surcharge. The beneficiary must request a review and provide the required information.

The Social Security Administration uses Form SSA-44 for requests involving certain life-changing events. Retirees who receive an IRMAA notice should examine their circumstances before assuming the additional premium cannot be changed.

It is also important to distinguish IRMAA from plan costs. Changing Medicare Advantage or Part D plans does not necessarily remove an income-related surcharge.

13. Avoid Confusing the Annual Deadline With Late Enrollment Penalties

Penalties
Source: Canva

Medicare late enrollment penalties are another area where timing matters. However, the annual December 7 deadline and the initial enrollment deadlines for Medicare Parts A and B are not the same.

A person first eligible for Medicare at 65 generally has a seven-month Initial Enrollment Period. Missing that window without qualifying coverage or a special enrollment right can lead to delayed coverage or penalties.

For Part B, the late enrollment penalty generally increases the monthly premium by 10% for each full 12-month period someone could have had Part B but did not enroll. In many cases, that additional amount continues for as long as the person has Part B.

Part D has a different rule. Someone who goes at least 63 consecutive days without Medicare drug coverage or other creditable prescription drug coverage after becoming eligible may face a penalty.

The Part D penalty is generally calculated using 1% of the national base beneficiary premium for each uncovered month. That additional amount usually continues for as long as the person has Part D coverage.

Employer Coverage Requires Special Attention

Some retirees maintain health or prescription coverage through an employer, former employer, union, or spouse. Certain arrangements allow people to delay aspects of Medicare enrollment without penalties, but the rules are not identical for every type of coverage.

Before joining a new Medicare drug plan, confirm how it would affect your existing benefits. In some cases, enrolling in a separate plan can interfere with valuable employer or union coverage.

Retirees should also keep notices confirming that existing prescription drug coverage is creditable. These documents can be important if Medicare later questions whether an enrollment penalty applies.

14. Consider the Medicare Prescription Payment Plan

Payment Plan
Source: Canva

For retirees taking costly medications, the timing of prescription expenses can create cash flow problems. The Medicare Prescription Payment Plan provides an option to spread eligible out-of-pocket prescription costs across monthly bills during the calendar year.

The program is voluntary and available through Medicare plans offering Part D coverage. It does not reduce the total amount owed for covered prescriptions or replace the annual Part D spending threshold.

Consider a hypothetical retiree who faces several expensive prescriptions early in the year. Spreading eligible costs over monthly payments may make budgeting easier than paying a large amount at the pharmacy all at once.

However, spreading costs across the year is not the same as receiving a discount. Before enrolling, compare this option with Extra Help and other available assistance programs that may actually reduce drug expenses.

15. Check Your Coverage Before Submitting an Application

Once you have narrowed your choices, the final review should focus on details that cannot easily be corrected after enrollment closes. This includes the exact plan, covered prescriptions, provider network, and expected annual expenses.

Use Medicare’s official Plan Finder to compare available options for your ZIP code. Enter your current prescriptions and preferred pharmacies to develop a more realistic estimate of annual drug spending.

You can enroll through Medicare’s official enrollment system, directly with a plan, or by calling 1-800-MEDICARE at 1-800-633-4227. Medicare also offers free counseling through State Health Insurance Assistance Programs, commonly called SHIP.

Keep Proof of Your Enrollment

After submitting an application, save the confirmation number and any documents showing the plan selected. Check that the application was received and that the expected effective date is January 1, 2027.

If you change Medicare drug plans during annual enrollment, the new plan generally replaces the old drug plan when the new coverage begins. Confirm the transition rather than canceling coverage unnecessarily and risking an interruption.

Be cautious about unexpected sales calls or requests for personal information. Use official Medicare contact information or a trusted plan representative when discussing enrollment details.

16. Your Final Medicare Checklist Before December 7

The easiest way to avoid overlooking an important item is to complete the review in a consistent order. Start with the documents you already have, then compare actual costs and coverage before making a final decision.

This checklist covers the highest-priority tasks for someone reviewing Medicare Advantage or Part D coverage for 2027. People facing a plan termination, employer coverage change, or Medigap decision may need additional steps.

PriorityWhat to ReviewAction Before December 7
1Annual Notice of ChangeIdentify 2027 plan changes
2Prescription listConfirm all medications and costs
3Pharmacy optionsCheck network and preferred pricing
4Doctors and hospitalsVerify participation in exact plan
5Total annual costsCompare premiums and out-of-pocket expenses
6Medicare and Medigap optionsReview eligibility before switching
7Financial assistanceCheck Extra Help and state programs
8Enrollment confirmationSave proof of the final selection

Completing these tasks will not guarantee that every medical expense is predictable. It will, however, make the decision more informed and reduce the chance of overlooking a known coverage or cost change.

If you need help, contact SHIP for free, unbiased Medicare counseling. It can be especially useful when comparing Original Medicare, Medicare Advantage, prescription drug plans, and state-specific Medigap protections.

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