Avoiding Medicare Enrollment Penalties: What You Need to Know Before You Sign Up

Missing a Medicare enrollment deadline can cost more than just convenience—it can trigger lifetime penalties that increase your premiums for years to come. The rules can be complex, especially if you’re still working or covered by an employer plan, which makes proactive planning essential.

Our guide, “Will I Avoid Medicare Enrollment Penalties?”, helps you determine when to enroll in Medicare Parts A, B, and D—and what happens if you delay. It breaks down key timelines such as the Initial Enrollment Period, Special Enrollment Period, and the General Enrollment Period, so you can make decisions with clarity and confidence.

You’ll also learn:

• When you can delay enrollment without penalty (and when you can’t)

• How employer coverage and retirement timing affect Medicare deadlines

• What to do if you’ve gone without “creditable coverage” for prescription drugs

• How the 10% Part B penalty and 1% Part D penalty are calculated

This checklist-style handout gives you an easy way to identify your situation and take action before penalties apply. Whether you’re approaching 65, still covered by an employer plan, or helping a spouse transition to Medicare, this resource simplifies the steps and helps you avoid expensive mistakes.

At LynnLeigh & Co., we help you connect healthcare choices with your broader retirement strategy—so your plan protects both your health and your wealth.