Don't Let Simple Mistakes Cost You

Enrolling in Medicare seems straightforward, but it's easy to make costly errors — especially if you're navigating the process for the first time. From missed deadlines to misunderstanding what your plan actually covers, these mistakes can result in coverage gaps, higher premiums, and unexpected medical bills. Here are seven of the most common pitfalls and how to sidestep each one.

Mistake #1: Missing Your Initial Enrollment Period

The problem: Many people assume they can enroll in Medicare whenever they're ready. In reality, you have a specific 7-month Initial Enrollment Period (IEP) around your 65th birthday. Missing it without a valid reason — like having employer health coverage — triggers permanent late enrollment penalties on your Part B and Part D premiums.

The fix: Mark your calendar six months before your 65th birthday and begin researching your options early. If you're still working and covered through an employer, confirm whether that qualifies you for a Special Enrollment Period before assuming you can delay.

Mistake #2: Assuming Medicare Is Free

The problem: While most people pay no premium for Part A, Parts B, C, and D all come with monthly premiums, plus deductibles and co-insurance. Entering retirement without budgeting for these costs can strain your finances.

The fix: Research current premium and deductible amounts on Medicare.gov, and factor healthcare costs into your retirement budget. Explore Medicare Savings Programs if your income is limited.

Mistake #3: Not Comparing Part D Plans

The problem: Many enrollees pick a Part D plan based on the lowest premium — without checking whether their specific medications are on the plan's formulary, or what tier they fall under.

The fix: Use the Medicare Plan Finder at Medicare.gov. Enter your exact prescriptions to compare total annual drug costs (premium + deductible + copays) across available plans in your ZIP code.

Mistake #4: Forgetting to Enroll in Part D When First Eligible

The problem: If you don't sign up for Part D when first eligible and don't have other creditable prescription drug coverage, you'll face a late enrollment penalty added to your premium for as long as you have Part D coverage.

The fix: Even if you don't currently take many prescriptions, consider enrolling in a low-cost Part D plan to avoid the penalty. The cost of a cheap plan is usually far less than the accumulated penalty.

Mistake #5: Ignoring the Annual Enrollment Period

The problem: Medicare plans can change their premiums, covered drugs, networks, and benefits every year. Staying in the same plan year after year without reviewing it could mean you're overpaying or missing out on better coverage.

The fix: Every fall, review the Annual Notice of Change your plan sends you. Compare your current plan to alternatives during the Annual Enrollment Period (October 15 – December 7). Switching takes only a few minutes and can save money.

Mistake #6: Misunderstanding What Medicare Covers

The problem: Many people are surprised to learn that Original Medicare does not cover routine dental, vision, or hearing care. Assuming these services are included can lead to unexpected out-of-pocket expenses.

The fix: Familiarize yourself with Medicare's coverage gaps before you need care. If dental, vision, or hearing is important to you, look into Medicare Advantage plans that bundle these benefits, or purchase standalone supplemental coverage.

Mistake #7: Waiting Too Long to Sign Up for Medigap

The problem: Medigap (Medicare Supplement) policies are sold by private insurers and help cover Original Medicare's out-of-pocket costs. The best time to buy Medigap is during your 6-month Medigap Open Enrollment Period, which begins the month you turn 65 and are enrolled in Part B. During this window, insurers cannot deny you coverage or charge higher premiums due to pre-existing conditions.

The fix: If you want a Medigap policy, apply during this one-time guaranteed issue window. Waiting until later means insurers may deny your application or charge significantly more based on your health history.

Final Tips for a Smooth Medicare Experience

  • Keep all Medicare correspondence and your Medicare card in a safe, accessible place.
  • Never share your Medicare number with unsolicited callers — Medicare fraud is a serious concern.
  • Contact your State Health Insurance Assistance Program (SHIP) for free, unbiased local counseling.
  • Use Medicare.gov as your primary source of information — it's always up to date.

A little preparation goes a long way. By avoiding these common mistakes, you can enter Medicare with confidence and make the most of your coverage.