5 Pitfalls to Avoid During Medicare Annual Enrollment


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Written by: Alice Stevens | Best Company Editorial Team

Last Updated: October 16th, 2020

Updated August 21, 2020.

Medicare Annual Enrollment for 2021 coverage runs October 15, 2020 to December 7, 2020. It's a good opportunity for people with Original Medicare to evaluate if a Medicare Advantage plan might be better and vice versa. It's also important to double-check your Part D prescription drug coverage for 2021.

2020 Medicare Annual Election Period Guide

We worked with MedicareFAQ to create this guide to help you be confident when you go through this year's Annual Election Period for Medicare.

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To make the most of Medicare Annual Enrollment, it’s a good idea to research and prepare. You should also be aware of pitfalls to avoid during the once-per-year enrollment period.

Here are five pitfalls that Medicare experts identified:

  • Not looking for changes
  • Not considering other plans
  • Not enrolling in Part D
  • Following ill-advised recommendations
  • Procrastinating

Not looking for changes

The saying “The more things change, the more things stay the same” does not apply to Medicare plans. When a Medicare plan is changed, the coverage is not the same. Insurance companies make changes to the coverage and costs each of their plans have. Double-checking to make sure your prescriptions are covered is important to do each year.

John Hill, Gateway Retirement President
“The biggest pitfall is assuming things are the same. Medicare seems to be always changing. The next pitfall is timing, you have from October 15 until December 7 to make your selections for your drug plan or Medicare Advantage plan. If you assume your Medicare Advantage plan or drug coverage is the same, you may be disappointed.”

Adam Hyers, Hyers and Associates, Inc
“Oftentimes, Part D plans will change their premiums and copays while also moving certain drugs into different (more expensive) tiers or out of formulary altogether.

By the time someone might realize this in January, it can be too late to do anything about it. Part D plans are required to send out an ANOC (Annual Notice of Changes) form for all Part D and Medicare Advantage plans, but sometimes they are lost or ignored.

Consumers should never assume their drug plan will stay the same year over year. They should contact their agent to make sure or double check their prescriptions using the Plan Finder tool at Medicare.gov. Enrolling the most suitable plan can save people hundreds of dollars or more for the next year.”

Danielle R. Plummer, PharmD Consultant Pharmacist
“Insurance companies are constantly changing their formularies, so just because a medication was on the lowest tier formulary this year, it may not be the next. If you are not comfortable using the internet, ask for help through local library, insurance brokers, and pharmacies. If a chain pharmacy does not have time to work with you, check with your local independent pharmacies.

Insurance contracts also change which pharmacy is their preferred provider year to year, so don't assume that the pharmacy you've been using will still have the lowest copays for your plan. Call your plan to ask which pharmacy is preferred. Also ask about copays at independent pharmacies and mail order options.”

Not considering other plans

As Medicare health plans change and your health situation changes, it’s important not to assume that your current plan will always be best for you. By considering all your plan options for Medicare Advantage and Part D, you’ll make sure that you’ve got a plan that meets your health and budgetary needs.

Anastasia Iliou, former Senior Content Manager for MedicarePlanFinder.com
“Some things you should avoid are not reviewing your benefits, not seeing an unbiased agent, not thinking about your network and your prescriptions, and not remembering to take both coverage AND costs into account. Seeing a licensed, unbiased agent is important to make sure that you are really enrolling in the right plan.”

Kathryn Casna, Eligibility.com
“Many plans change each year, so look for your plan's Annual Notice of Change (ANOC) in the mail in October, and make sure the plan still meets your needs. On the flip side, it never hurts to call an agent or run your info through the plan finder at Medicare.gov each year to see if you can get a better plan or a lower price elsewhere.”

Not enrolling in Part D

Medications and prescriptions are important, especially if you rely on a daily medication. If you don’t currently take medications, it may not make sense to enroll in prescription drug coverage. But, if you eventually do need medication and have not had prescription drug coverage, your costs may be higher down the road.

Alex Enabnit, Eligibility.com
“If you don’t have drug coverage but anticipate needing it at some point in the future, find a Part D plan during AEP. If you know you’ll never want drug coverage, that’s fine. But if at some point you will, you need to know that Medicare enforces a penalty charge for every month you went without drug coverage. This penalty remains in force, monthly, for the rest of your life. Yes, you read that right. Avoid this pitfall!”

Following ill-advised recommendations

Lots of people get advice from family members and friends for some major life decisions. While it’s nice to have a good support network, it’s important to realize that everyone’s health and financial situation is different. A plan that worked well for your friend may not be great for you.

Kathryn Casna, Eligibility.com
“Medicare beneficiaries will get tons of recommendations this season, but unless those recommendations are closely matched to your individual situation, you could be enrolling in the wrong plan. Both of these pitfalls can be side-stepped with a bit of research into the plans that fit your individual needs.”


Don’t underestimate how long the underwriting and approval process can take when enrolling in a new Medicare plan. You’ll want to know if your application has been declined with plenty of time to apply for another.

Danielle K. Roberts, Boomer Benefits
“It’s important to start early. Don’t procrastinate until the end of the enrollment period because both insurance companies and Medicare get swamped with applications. There are longer hold times if you call in with a question. You also need adequate time to research your options so that you are not rushing to choose a plan.

Another pitfall can occur if you are wanting to disenroll from a Medicare Advantage plan and return to Original Medicare and add a Medigap plan. In most cases you must answer health questions on the application for Medigap and the insurance company needs to time to decide whether they will accept for decline you. So it’s important that you apply for the Medigap plan first and well in advance of the December 7th deadline. Don’t cancel your Medicare Advantage plan until you have received approval from the Medigap carrier that they are granting you a policy.”

Avoiding pitfalls

Avoiding these Medicare Annual Enrollment pitfalls will help you find an affordable plan that meets your coverage needs. Reviewing any changes, double-checking prescription coverage and costs, and applying early in the enrollment period will help you decide if it's best to stick to your current plan or make a change.

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