Enrollment Guidance

Medicare

Enroll at the right time and you avoid penalties for life.

Medicare has deadlines, and several of the penalties for missing them are permanent. Whether you are turning 65, retiring later, or leaving employer coverage, the timing question comes before the plan question.

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The Basics

Your situation decides your deadline.

Someone retiring at 65 follows a different path from someone still working at 68 with employer coverage, or someone on a spouse’s plan, or someone on COBRA. Each has different windows and different consequences for getting it wrong.

The most common expensive mistake is assuming COBRA or retiree coverage counts the same as active employer coverage. It often does not, and the resulting Part B penalty is permanent.

Turning 65 with or without employer coverage
Retiring after 65 and leaving a group plan
Moving to a new county or state
Reviewing your plan during Annual Enrollment

Start Early

Come talk to us three to six months before you turn 65 or before you plan to retire. There is no cost, no obligation, and starting early is the difference between choosing a plan and scrambling to meet a deadline.

What We Help With

Getting the timing right

Turning 65

Your initial enrollment window, and whether to take Part B now or defer it.

Still Working

Whether your employer plan lets you delay without a penalty, which depends on employer size.

Leaving Group Coverage

The special enrollment period that opens when active employer coverage ends.

Annual Enrollment

The fall window to change Advantage or Part D plans for the coming year.

Avoiding Penalties

Part B and Part D late enrollment penalties, both of which can last for life.

Moving

Advantage and Part D plans are county-specific, so a move can require a change.

Common Questions

Enrollment FAQs

When should I start looking at this?

Three to six months before you turn 65, or before you retire if that is later. Early conversations are free and give you time to compare rather than react to a deadline.

I’m still working. Do I have to enroll at 65?

Not always. It depends on your employer’s size and how their plan coordinates with Medicare. Getting this wrong in either direction is costly, so it is worth confirming rather than guessing.

Does COBRA count as creditable coverage?

Generally not the way active employer coverage does, and relying on it is one of the most common causes of a permanent Part B penalty. Talk to us before you make that assumption.

What does your help cost?

Nothing. Agents are compensated by the carriers, and plan pricing is set by CMS, so enrolling on your own does not save you money.

Turning 65 or retiring soon?

Come talk to us early. There is no cost and no obligation.

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