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 mistakes^✱ to watch out for, and how to avoid them.

^✱ 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 Medicare Part B because they have employer health coverage. At age 65, an employer plan generally pays first when the employer has 20 or more employees, while Medicare pays first when the employer has fewer than 20 employees. Delaying Part B when Medicare should pay first can leave you with unpaid medical bills. If you do not qualify for a Special Enrollment Period, Medicare may add a 10% penalty for each full 12-month period you delayed enrollment, and the penalty usually continues for as long as you have Part B.

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 coverage through your or your spouse’s current employment, you may delay Part B without a penalty, but you must enroll within 8 months after the employment or coverage ends, whichever happens first.

2. Counting on COBRA or Retiree Coverage to Delay Medicare

COBRA and retiree coverage may seem like a bridge to Medicare, but they do not count as coverage based on current employment for the Part B Special Enrollment Period. Your 8-month enrollment window begins when active employment or employer coverage ends, whichever happens first—even if you choose COBRA. Delaying Part B can lead to unpaid medical bills, a coverage gap, and a late enrollment penalty.

How to avoid it:

Once your active employment ends, sign up for Medicare Parts A and B promptly – even if you’re offered COBRA or retiree coverage. This helps ensure Medicare becomes your primary insurance and protects you from coverage gaps or late enrollment penalties.

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 63 days or more without creditable prescription drug coverage after becoming eligible. That penalty is 1 percent of the national base beneficiary 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.