If you miss Medicare enrollment deadlines, the cost can follow you for years. The Part B late enrollment penalty is 10% of the standard Part B premium for every full 12-month period you delayed enrollment, and it usually lasts as long as you have Part B. The Part D late enrollment penalty is 1% of the national base beneficiary premium for each full month you went without Part D or other creditable drug coverage; it generally lasts as long as you have Part D coverage. People who keep working past 65, rely on COBRA or retiree coverage, or assume every employer plan lets them delay Medicare are among those most at risk.

For people approaching Medicare in Pennsylvania, these rules can feel unforgiving—but they do not have to be confusing. At WitcherWay Wellness, we review every client’s enrollment window before any enrollment decision is made, so the decision is based on the person’s actual coverage, employment situation, and timing.

Understanding the Initial Enrollment Period

Your Initial Enrollment Period is the first major Medicare deadline to know. For most people turning 65, it lasts seven months: the three months before the month you turn 65, your birthday month, and the three months after it.

During this period, you can enroll in Medicare Part A and Part B. If you need prescription drug coverage, this is also the time to consider a Medicare Part D plan or a Medicare Advantage plan that includes drug coverage. Missing this window does not automatically mean you will owe a penalty—but it does mean you need to know whether you have coverage that allows you to delay correctly.

This is especially important for those researching Medicare enrollment in Pennsylvania while still employed. A job-based health plan may change the answer, but the name of the plan alone is not enough. Details matter.

How the Part B Late Enrollment Penalty Works

Part B covers outpatient and medical services, such as doctor visits, preventive care, lab work, durable medical equipment, and many other services outside a hospital stay. If you could have enrolled in Part B and did not have a valid reason to delay, your monthly Part B premium can increase by 10% for each full 12-month period you went without it.

For example, a person who delays Part B for two full years without qualifying for a Special Enrollment Period may pay a 20% penalty in addition to the standard monthly Part B premium. That is not a one-time fee. In most cases, it stays in place for as long as the person has Part B.

The biggest concern is not simply the first year of the penalty. It is the ongoing cost and the possibility of delayed access to coverage while waiting for an available enrollment period. Ralph Witcher helps clients slow down, ask the right questions, and make a clear decision before a deadline is missed.

How the Part D Late Enrollment Penalty Works

Part D helps cover prescription drugs. The penalty is calculated differently from Part B: Medicare multiplies 1% of the national base beneficiary premium by the number of full months you were eligible but went without Part D or other creditable prescription drug coverage. The result is rounded and added to your monthly Part D premium.

For 2026, the national base beneficiary premium is $38.99. A person with 14 full uncovered months, for example, would have a 14% penalty calculation before rounding. Because the national base beneficiary premium can change each year, the dollar amount of the penalty can also change.

The key word is creditable. Employer or union drug coverage is not automatically creditable just because it includes prescriptions. The plan should provide a creditable coverage notice telling you whether its drug benefits are expected to pay, on average, at least as much as standard Medicare Part D coverage. Keep that notice with your important Medicare records.

The Most Common Mistakes That Trigger Penalties

Most late enrollment penalties are caused by an understandable assumption rather than an intentional decision to skip coverage. Common mistakes include:

• Assuming COBRA protects your Part B enrollment rights. COBRA is not current-employment coverage for the standard Part B Special Enrollment Period. Waiting until COBRA ends can leave someone with a late enrollment penalty or a coverage gap.
• Confusing retiree health coverage with active employer coverage. Retiree plans may coordinate with Medicare differently and often do not allow a penalty-free Part B delay.
• Not checking employer size. Whether the employer has 20 or more employees can affect who pays first and whether delaying Part B is practical and safe.
• Failing to verify Part D creditability. A person may properly delay Part B but still create a Part D penalty if their prescription coverage is not creditable.
• Missing the deadline after work or coverage ends. The enrollment clock starts sooner than many people expect.

Delaying Medicare Correctly vs. Delaying Incorrectly

A correct delay is usually based on coverage through your own or your spouse’s current employment and a group health plan that supports the decision. When that coverage ends—or when the employment ends, whichever happens first—you generally have an eight-month Special Enrollment Period to enroll in Part B without a late penalty. This window does not wait for COBRA to end.

For Part D, the goal is to avoid going 63 days or more without Medicare drug coverage or other creditable prescription drug coverage. If you are leaving an employer plan, ask for the drug coverage notice and confirm whether a Medicare drug plan needs to begin immediately.

An incorrect delay happens when someone treats any health coverage as though it were active employer group coverage. COBRA, Marketplace coverage, retiree coverage, and a spouse’s coverage after the spouse has stopped working can all require closer review. The safest approach is to evaluate the coverage before declining or postponing Medicare.

Why Employer Plan Size Matters

For people eligible for Medicare because of age, an employer with 20 or more employees will generally have a group health plan that pays first while the employee remains actively covered through current employment. In that situation, delaying Part B may be appropriate if the rest of the coverage and cost analysis supports it.

With a smaller employer—generally fewer than 20 employees—Medicare may pay first. The employer plan may expect Medicare to cover its share, meaning delaying Part B can expose you to unpaid bills or limited coverage. Many small-employer and retiree plans require eligible members to enroll in both Part A and Part B when first eligible.

That does not mean every situation fits a simple rule. Employer arrangements, spouse coverage, Health Savings Account contributions, disability status, and plan documents can all affect the best next step. WitcherWay Wellness takes a relationship-centered approach: we review your enrollment window before any enrollment decision is made and explain the options in plain language.

Get Guidance Before You Make an Enrollment Decision

Medicare penalties are often avoidable, but only when timing and coverage are reviewed early enough. If you are turning 65, working past 65, retiring, losing employer health insurance, or helping a parent make a Medicare decision, start with a conversation rather than an assumption.

Explore our Medicare Guidance resources and our overview of Employer Coverage to Medicare. WitcherWay Wellness serves individuals and families throughout Pennsylvania with clear, compassionate support designed to move people from uncertainty to confidence—one important decision at a time.

FAQ

Does the Part B late enrollment penalty ever go away?

In most cases, no. The Part B penalty generally continues for as long as you have Part B. Qualifying for a Special Enrollment Period can help you avoid the penalty when you enroll after your Initial Enrollment Period.

Can I delay Part D if I do not take prescription medications?

Possibly, but going without Part D or other creditable drug coverage for 63 days or more can trigger a penalty later. Whether you currently take medications is not the only issue; the coverage timeline matters.

Is COBRA considered active employer coverage for Medicare enrollment?

No. COBRA can be valuable coverage, but it does not extend the standard Part B Special Enrollment Period tied to current employment. Review your Medicare timeline before choosing COBRA or relying on it after age 65.

What should I ask my employer before delaying Medicare?

Ask whether the coverage is based on current employment, how many employees the employer has, whether the health plan pays before Medicare, whether drug coverage is creditable, and what documentation you will receive when employment or coverage ends.

How can WitcherWay Wellness help?

Ralph Witcher and the WitcherWay Wellness team can help you understand your timing, compare your coverage options, and identify questions to take to your employer or benefits administrator. Schedule your free enrollment review today before making an enrollment decision.