5 Medicare Mistakes to Avoid at 65 in Massachusetts

Navigating your Medicare choices at 65 in Massachusetts can feel overwhelming, and a few early missteps can have lasting financial consequences. From enrollment timing to understanding what coverage you actually need, several common mistakes catch new enrollees off guard each year.

The good news? These pitfalls are easy to avoid when you know what to look for. By planning ahead and making informed decisions, you can steer clear of late penalties, network surprises, and coverage gaps. Here are five mistakes¹ to watch out for, and how to avoid them.

¹ These five mistakes reflect patterns consistently highlighted in public Medicare education materials for Massachusetts residents, including guidance from state-published enrollment guides and CMS fact sheets.

1. Assuming No Penalties by Delaying Part B

Many people delay signing up for Medicare Part B, thinking they don’t need it yet. But if you’re not actively covered by a large employer group plan (typically 20 or more employees), waiting past your Initial Enrollment Period can result in a permanent late enrollment penalty. Medicare adds a 10 percent surcharge for each full year you delay, and that penalty applies for life.

How to avoid it:

Enroll in Part B during your 7-month Initial Enrollment Period, which starts 3 months before the month you turn 65 and ends 3 months after. If you have large-group employer coverage, you can delay Part B without penalty, but you must enroll within 8 months of losing that coverage.

2. Counting on COBRA or Retiree Coverage to Delay Medicare

COBRA and retiree health benefits may seem like a good bridge to Medicare, but they are not considered primary coverage once you become eligible for Medicare. If you delay enrolling in Part B while relying on these plans, you could be left with unpaid medical bills and face lifetime late penalties.

How to avoid it:

Once your active employment ends, sign up for Medicare Parts A and B within 8 months, even if you’re offered COBRA or retiree coverage. This ensures Medicare becomes your primary insurance and protects you from coverage gaps or penalty fees.

3. Skipping Part D Because You Don’t Take Prescriptions

If you’re not currently on any medications, it may feel unnecessary to enroll in drug coverage. But Medicare charges a late enrollment penalty if you go more than 63 days without creditable prescription drug coverage after becoming eligible. That penalty is 1 percent of the national base premium for every uncovered month, and it applies for as long as you have Part D.

How to avoid it:

Select at least a basic, low-cost Part D plan during your Initial Enrollment Period. Even if you don’t use it now, you’ll avoid future penalties and be protected if your prescription needs change later.

4. Believing You Cannot Switch Medigap Plans Later

Some new enrollees worry they’ll be locked into their Medigap choice, so they either overpay for extra coverage or stick with a plan that doesn’t fit. In Massachusetts, this concern is often unfounded.

How to avoid it:

Take advantage of Massachusetts’ year-round Medigap switching rights. You can change from Core to Supplement 1A – or switch insurers – any month of the year, with no health questions or underwriting. Choose the plan that fits your needs today, knowing you can adjust your coverage later if needed.

5. Assuming All $0 Premium Medicare Advantage Plans Are Alike

A $0 premium may sound appealing, but not all Medicare Advantage plans offer the same value. Some have limited provider networks, higher copays, or drug formularies that don’t cover the medications you need. Choosing a plan without comparing details can lead to unexpected out-of-pocket costs or restricted access to care.

How to avoid it:

Look beyond the premium. Review each plan’s network, copay structure, and prescription coverage. Confirm that your doctors and medications are included, and use tools like the Medicare Plan Finder or speak with a licensed agent to compare options thoroughly.

Take the Next Step with Confidence

Avoiding these common Medicare mistakes can save you time, money, and frustration – especially in a state like Massachusetts, where some rules work differently than elsewhere. With the right information and a little planning, you can make confident decisions that protect your coverage and your wallet from day one.

At Hesteon Solutions, we specialize in guiding Massachusetts residents through the Medicare process. Whether you are comparing plans, unsure about your enrollment timing, or need help understanding your options, we are here to help – at no cost to you.