Medicare Enrollment Help

Enrolling in Medicare can feel overwhelming, but it doesn’t have to be. At Capstone Insurance and Financial Group, we help you enroll at the right time and avoid costly mistakes or penalties.

There’s a right way and a right time to enroll in Medicare.

Whether you’re turning 65, retiring soon, or qualifying due to a disability, Medicare has specific enrollment periods and rules. Missing a deadline or enrolling in the wrong parts can lead to coverage delays or late penalties.


We walk you through your Initial Enrollment Period, explain the difference between Open Enrollment and Special Enrollment, and help you complete the paperwork correctly and on time. With our guidance, you can enroll with confidence and clarity.

Step-by-Step Guidance Through Every Period

From your first enrollment to annual reviews, we help you understand what each window means and how to take action.



Avoid Mistakes and Missed Deadlines

Late enrollment can mean gaps in coverage or lifetime penalties. We make sure you enroll at the right time to avoid unnecessary costs.


Get Help Tailored to Your Situation

Whether you’re retiring, working past 65, or helping a spouse enroll, we guide you based on your exact needs and timeline.


Frequently Asked Questions

  • When should I enroll in Medicare for the first time?

    Your Initial Enrollment Period starts three months before you turn 65 and lasts for seven months total. We help you determine your exact timeline.

  • What happens if I miss my Initial Enrollment Period?

    You could face delays and lifetime penalties, depending on your situation. We help you find the best way forward.

  • Can I enroll if I’m still working at 65?

    Yes, but the timing depends on your employer coverage. We help you decide whether to enroll now or delay.

  • What is the Medicare Open Enrollment Period?

     It’s the time each year—October 15 to December 7—when you can change your Medicare Advantage or Part D plan.

  • Is enrollment automatic?

     It may be automatic if you’re already receiving Social Security benefits. If not, you’ll need to enroll manually—and we’ll help you do it right.

The right timing can make all the difference.

Let us walk you through your Medicare enrollment step by step.

From your first sign-up to annual changes, we make Medicare enrollment stress-free and simple.