4 expert tips for signing up for Medicare

By Robert Powell

A day in the life of a Medicare counselor

The stakes are high and there's plenty of uncertainty.

It is perhaps one of the cruelest things millions of older Americans are subjected to each and every year between Oct. 15 and Dec. 7: reviewing and updating their Medicare Advantage and Part D prescription drug plans for the coming year.

During this year's open-enrollment period, beneficiaries have to contend with many changes. I was able to observe several appointments my senior center's SHINE counselor recently had with Medicare beneficiaries.

Throughout the country, more than 11,000 counselors, commonly known as SHIP counselors (this stands for state health insurance assistance program), help Medicare beneficiaries sort through their options and find coverage that works for them. In Massachusetts, where I live, they're called SHINE counselors.

The stakes are high. Medicare Advantage and Part D prescription drug plans can change from one year to the next. Premiums, deductibles, copayments and coinsurance can rise. Provider networks can shrink, and formularies - the lists of drugs a plan covers - can change. For older Americans living on fixed incomes, those changes can take a bite out of an already stretched budget.

And then there's the uncertainty of what lies ahead. No one knows what health problems they might face in the coming year, whether they'll need a new specialist or be prescribed expensive medication. A plan that works well today might not meet their needs tomorrow.

Yet despite the stakes, 69% of Medicare beneficiaries didn't compare their coverage to other available options during open enrollment for 2022, according to a 2024 KFF analysis.

Perhaps that's not surprising. Comparing plans is complicated, and it's often easier to stick with what you have than to sort through all the alternatives.

But doing nothing can come at a price. You could end up paying more than necessary for coverage that no longer meets your needs.

The average appointment with a SHIP counselor takes 30 minutes, and because the counselors are supported through federal funding, their help is provided free of charge and they receive no commissions or other financial incentives from Medicare Advantage and Part D plans. That means that unlike insurance brokers who receive a commission for their recommendations, they must offer unbiased support and not steer anyone toward a particular plan.

Given all that, many Medicare experts routinely recommend that beneficiaries schedule appointments with these counselors, who receive extensive training.

But knowing that counselors are well-trained is one thing. Watching them put that training to work is quite another.

What I witnessed was equal parts financial detective work, problem-solving and lots and lots of patience. And, frankly, something approaching God's work.

The first two appointments, involving a husband and wife, were relatively straightforward. This is typically the case when beneficiaries are prepared with their Medicare.gov accounts, know their usernames and passwords, have an up-to-date list of their prescription drugs and can verify that the medications Medicare has on file match what they're actually taking.

The wife had all that information at her fingertips.

The husband wasn't quite as prepared. He couldn't remember which email address he'd used to set up his Medicare.gov account, and he wasn't sure what his password was.

But once that was resolved, the task was relatively simple: Find the Part D prescription drug plan with the lowest total annual cost, including premiums and out-of-pocket expenses, given that both were taking inexpensive, commonly prescribed generic medications.

In the end, both chose a plan that offered the lowest total annual cost for their medications and carried a monthly premium of $13.30, down from $16.40 in 2026.

But don't mistake those relatively straightforward appointments for evidence that the Part D marketplace is simple.

Fewer plans are available for 2027, most beneficiaries with stand-alone drug coverage face higher premiums if they stay in their current plans, and deductibles are increasing, according to KFF. And the exact drugs a person takes, how a plan covers them and which pharmacy they use can make a substantial difference.

Bottom line: The plan with the lowest premium isn't necessarily the plan with the lowest cost. And the plan that worked best this year may not be the best one for next year.

The next appointment was a bit more complicated. For starters, the beneficiary was enrolled in MassHealth, Massachusetts' Medicaid program, and a Medicare Savings Program known as Qualified Medicare Beneficiary, or QMB. The program helps people with limited incomes pay Medicare premiums, deductibles and other Medicare cost-sharing expenses.

The beneficiary's Medicare Advantage PPO plan from Mass General Brigham Health Plan, which included Part D prescription drug coverage, was discontinued for 2027.

And the beneficiary wasn't quite sure which, if any, prescription drugs he was taking.

So the counselor had to find replacement medical and prescription drug coverage that would work with the beneficiary's MassHealth and Medicare Savings Program benefits.

In the end, after some hunting around in Medicare.gov's Plan Finder tool, the counselor recommended that the beneficiary enroll in Mass General Brigham Advantage Core (HMO-POS). The plan would allow him to continue seeing his primary-care physician and specialists, all of whom were in the plan's network, while also providing additional dental, hearing and vision benefits.

Before enrolling, however, the counselor had to walk the beneficiary through the plan's fine print. The beneficiary, who remained in good humor despite the complications, learned about the plan's limitations on coverage outside the U.S. and that he generally would have to use doctors and other providers in the HMO's network.

He also needed reminding that he could continue using his current plan through the end of the year, with his new coverage taking effect Jan. 1. For good measure, the counselor attached a Post-it note to his old insurance card as a reminder.

Watching all this unfold, I came to appreciate that no detail, however small, could be overlooked.

Another beneficiary faced a different problem. She had MassHealth coverage and qualified for Extra Help, the federal program that reduces Medicare prescription drug costs. But her stand-alone Part D prescription drug plan, Aetna's SilverScript Choice, was being discontinued for 2027, forcing her to shop for replacement coverage.

Things were bumpy from the start. The counselor couldn't log in to the beneficiary's Medicare.gov account. And the reason was enough to confound just about anyone.

As if finding the right Medicare plan weren't complicated enough, beneficiaries first have to figure out how to get into their own accounts. And that's no small task if they can't remember which login method they used, much less their username and password.

There are several ways to sign in to Medicare.gov, including through ID.me, Clear, Login.gov or directly through Medicare.gov. After several unsuccessful attempts, the counselor finally gained access using the beneficiary's Login.gov account.

The beneficiary had come prepared with a list of prescription medications, but none were recorded in Medicare.gov's system. So once logged in, the counselor had to enter each drug manually.

And here's something I learned: It matters whether a medication comes in tablet or capsule form. The same drug can cost more in one form than the other.

With the medications finally entered, the counselor began the time-consuming task of comparing Part D plans, including Humana Basic Rx Plan and Blue MedicareRx Value Plus, along with their star ratings.

That meant looking beyond monthly premiums to compare total annual costs, including deductibles and prescription drug expenses, as well as checking pharmacies. A pharmacy might be preferred in-network under one plan, but standard in-network or out of network altogether under another. And those distinctions can make a difference in what a beneficiary pays.

In the end, the beneficiary chose the same plan through which she was already filling all her prescriptions.

But the counselor's work wasn't finished. There was still the enrollment process, the fine print to read aloud and a series of questions about whether the beneficiary wanted to receive information by email or regular mail, in standard print or large print, and so on.

Mind-numbing stuff, to be sure. But the counselor treated every question as though it mattered. Because, of course, it did.

This was the last appointment I witnessed, and it reinforced something I've recommended to readers for years: When it comes to Medicare's annual election period, preparation matters. Keep these things in mind when preparing to make your selection for next year:

-- Read your annual notice of change.

-- Know your Medicare.gov username and password, if you still use them, and which method you use to log in.

-- Have an up-to-date list of your prescription medications, including dosages, and the names of your doctors.

-- Schedule an appointment with a SHIP or SHINE counselor sooner rather than later. And these appointments are valuable, so show up on time or cancel with enough notice to give someone else a chance to get help.

What stayed with me most was an exchange between the counselor and a beneficiary near the end of an appointment.

"These plans keep changing every year," the counselor reminded the beneficiary.

"You mean I have to keep doing this every year?" the beneficiary asked.

Yep. Every year.

-Robert Powell

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