How to Build a Medicare Enrollment Checklist

As if it needed to be said: healthcare is notoriously confusing. We’ve all felt the stress of selecting the right provider, the right plan, and the right coverage—well, Medicare is no different. With multiple plan options and enrollment windows, it would almost be easier to have a simple, easy-to-follow Medicare enrollment checklist to ensure that you can make a healthcare decision you’re confident in, right?

Well you’re in luck—Healthpilot is here to run through everything you need to include in your checklist so you can get the coverage you need.

Why Do I Need a Medicare Enrollment Checklist? If you’re not convinced, there are several reasons to have a Medicare enrollment checklist created before beginning the process of enrolling in Medicare:

Choosing the Right Medicare Plan for Your Needs : Depending on your age, job status, and health needs, your enrollment timeline and coverage options may vary. Avoiding Penalties : Late enrollment can increase your monthly premiums for Part B and Part D coverage in particular. Knowing Enrollment Deadlines : There are various Medicare enrollment periods . Be sure that you know when you’ll be eligible for enrollment or renewal based on your unique situation. Comparing Plans Confidently : Using tools like Healthpilot’s platform effectively means having all necessary information on hand—a Medicare enrollment checklist helps keep you organized. Medicare Basics to Know Before Building Out Your Checklist Though enrollment periods and specific coverage details (like premiums, out-of-pocket expenses, and deductibles) may vary year over year and plan by plan, there are a few constants to keep in mind and include in your checklist.

The Basic Requirements for Original Medicare Most individuals qualify for Medicare when they are about to turn 65 (or earlier, due to a qualifying disability or end-stage renal disease). The Medicare enrollment process typically requires the following:

U.S. citizenship or legal residency for at least 5 years Eligibility to receive benefits from the Social Security Administration or Railroad Retirement Enrollment in Medicare through the Social Security Administration website The Initial Enrollment Period (IEP) Another basic to keep in mind is that your Initial Enrollment Period (IEP), though unique to you based on your birth date, follows the same structure for every individual:

Starts 3 months prior to the month in which you turn 65 Includes the month in which you turn 65 Ends 3 months after the month in which you turned 65 Enroll for Part B or Part D coverage during this window to avoid incurring penalties.

Consult With Healthpilot

Your Medicare Enrollment Checklist Now that we’ve established the basic information you need to know about enrolling in Medicare, let’s run through a comprehensive enrollment guide.

Step 1: Know Your Enrollment Period Here’s a quick breakdown of the various Medicare enrollment periods you may be eligible for:

Initial Enrollment Period (IEP) : Begins 3 months before you turn 65, includes the month in which you turn 65, and ends 3 months later Special Enrollment Period (SEP) : Can happen anytime before or after you turn 65, but must be triggered by a specific circumstance . Annual Enrollment Period (AEP) : Between October 15th and December 7th each year. Open Enrollment Period (OEP) for Medicare Advantag e: Between January 1st and March 31st each year. General Enrollment Period (GEP) for Original Medicare : Between January 1st and March 31st each year, for those who missed their IEP or SEP. If you need a deeper explanation on Medicare enrollment periods, check out Healthpilot’s guide to Medicare enrollment periods .

Step 2: Gather Your Personal Information Whether you’re enrolling in Part B or Part D through the Social Security Administration, or using a Medicare plan finder tool like Healthpilot, there is a set list of personal and medical information you should have on hand before you begin the process:

Social Security Number or My Social Security account information. If applicable, the date that your employer’s health insurance ends . For more on switching from employer-provided health insurance to Medicare, read our guide . W-2s and other tax documents . These will be used to verify your income for premium adjustments. A list of the prescriptions you are currently taking , as well as any that you are expecting to take in the future. Be sure that this list includes the dosage and frequency of each medication. A list of your current doctors and preferred pharmacies in your area. Step 3: Understand Your Coverage Options There are various parts of Medicare that cover different things, some of which can be combined or changed to get the best coverage for your unique healthcare needs:

Think of Medicare Part A as “hospital insurance”. It covers inpatient hospital stays, hospice, and skilled nursing. Medicare Part B is akin to traditional medical insurance, covering outpatient care, doctor visits, and preventive care. Together, Medicare Parts A and B make up Original Medicare . You may see this term used throughout the enrollment process. Private insurance carriers that have been approved to offer Medicare plans offer Medicare Part C (also known as Medicare Advantage). This plan is an alternative to Original Medicare, and often offers additional coverage (such as vision, dental, hearing, or prescription drugs). Medicare Part D (sometimes also called the PDP part of Medicare) provides coverage for prescription drugs. Medigap , or Medicare Supplement Insurance , is offered by private insurance carriers as a way to cover costs not paid for by Original Medicare. Step 4: Compare Medicare Plans As you compare what coverage options will work best for you, another tool that will help is Healthpilot. We make it easy to compare Medicare plans based on the following:

Monthly Premiums : See how much you’ll be paying monthly, or set a budget of your own for our recommendations to stick within. Deductibles & Co-Pays : Know exactly how much you’ll be paying out-of-pocket, whether you’re visiting the doctor, seeing a specialist, or getting testing. Prescription Drug Coverage & Formulary : Confirm that your medications will be covered and how much they’ll cost. Provider & Pharmacy Networks : Keep care convenient by entering your preferred doctors, specialists, pharmacies, and hospitals. Extra Coverage : Looking for plans with additional benefits? We’ve got you covered. Star Ratings : Get an idea of plan and carrier quality, as well as customer satisfaction. But it doesn’t stop there—Healthpilot also provides direct recommendations for plans that meet your healthcare needs, allows for seamless signup within our platform, and acts as your support and guide moving forward.

Get Started With Healthpilot

Step 5: Make Your Coverage Selection Once you’re confident in the Medicare coverage you will need, it’s time to kick off the enrollment process:

Visit the Social Security Administration website to enroll in Medicare Part B (and A, if applicable) If you’re planning on using Healthpilot: Have your Medicare card on hand and visit our website to get started—we take you through the process of comparing Medicare plan options step-by-step If you’re not planning on using Healthpilot: Choose which coverage you may need (Medigap or Medicare Advantage, prescription drug plans) If you choose Original Medicare, you may add Part D coverage for prescription drugs If you qualify for assistance, apply for Extra Help Confirm the start date of your new Medicare plan Step 6: Coordinate Coverage Start & End Dates If you’re currently enrolled in Marketplace or employer-sponsored coverage, connect with your employer, HR department, or benefits provider to notify them of the upcoming switch. This ensures that:

There is no conflicting coverage You are not paying double premiums There is no gap in coverage during the transition Step 7: Keep Your Documents Safe As with any other official documents, be sure that you store your Medicare information in a secure place. These documents include:

Your Medicare card (once received) Your Medicare number The Welcome to Medicare packet and your plan confirmation letter The password and username for your MyMedicare account What Are the Biggest Mistakes People Make With Medicare? Even if you’re experienced with Medicare, mistakes can still happen. Being aware of them now ensures you can avoid them. Here are some common mistakes people make when enrolling in Medicare:

Not coordinating employer-provided coverage with Medicare, resulting in coverage gaps, double premiums, or conflicting coverage Enrolling in a Medicare plan without ensuring that your preferred doctors, pharmacies, and prescriptions are covered Not enrolling in Medicare Part D (prescription drug coverage) when it’s needed Foregoing annual plan reviews during the OEP and AEP

Do I Need to Do Anything During Medicare Open Enrollment? Once you’ve made the initial enrollment into Medicare, you won’t be required to do anything during the Annual Enrollment Period (AEP) and Open Enrollment Period (OEP).

However, it’s true that Medicare plans change annually. Healthpilot recommends that you r eview your coverage during the Annual Enrollment Period or Open Enrollment Period . As your trusted Medicare resource, Healthpilot is here to ensure that you’re:

Enrolled in the best plan available for your needs During the OEP, you can switch Medicare Advantage plans or return to Original Medicare During the AEP, you can switch to Medicare Advantage plans, enroll in Medicare Advantage from Original Medicare, or change, add, or remove Medicare Part D Not overpaying for coverage Utilizing your benefits to their fullest Get Started With Healthpilot

Healthpilot: An Extension of Your Medicare Enrollment Checklist

Don’t navigate through Medicare enrollment alone—Healthpilot is here to help you by:

Comparing plans that match your prescriptions, doctors, and budget Recommending the best available solution for your needs with no sales pressure Enrolling online takes under 15 minutes Reminding you of enrollment windows before they begin Acting as a liaison between you and Medicare plan, helping with appeals and coverage questions Got your checklist in hand and feeling ready to get started? We are too! Click here to get the right Medicare plan for you.

How to Build a Medicare Enrollment Checklist

Medicare Part D Deductible 2025: Changes and Cost Breakdown

Medigap Plans Cost in 2025 + Factors That Affect Pricing

We're Here to Help with Any Questions

Talk to an Agent

Chat Online

Send Us an Email