I turned 65 in April 2025, and I’m still working with my employer’s high deductible health plan. I reached out to Medicare for guidance on enrollment, and they advised me against signing up for Part A for now, even though it’s free. They also suggested I shouldn’t enroll in Part B or D, mentioning that if I lose my employer’s coverage, I’d then automatically get Part A. There’s a grace period of a month, apparently, for registration. I’m planning on registering for Part B anyway.
However, a coworker mentioned that I shouldn’t have to sign up for Part B, but I’ve heard mixed signals about it. Should I have enrolled in Parts A and B, and maybe even D? I’m worried—will I face an IRMAA penalty for missing the seven-month enrollment period that includes my birthday? Can a financial planner, like, help seniors figure out this stuff, or is hiring one only necessary if I have other financial issues? Who’s the right person to talk to?
In response, it seems like you were correct in not enrolling just yet. If you’re still working and covered by your employer’s high-deductible plan, it’s generally wise not to jump into Medicare Part A or B right away, according to Max Coupland, CEO of Insuranceopedia. Enrolling in Part A means you can’t contribute to an HSA, and Part B premiums are unnecessary while your employer’s insurance is your primary source. About the late enrollment penalty, as long as you sign up for Part B within eight months after losing your employer coverage, you should be fine. And those IRMAA surcharges? They’re assessed based on your income at the time you enroll, not when you apply.
According to Anthony Ogorek, a certified financial planner, Medicare will send you a welcome letter with your Part A card as you near 65. Depending on your employer’s health insurance costs and quality, it might be best to stick with it until retirement or when you start receiving Social Security benefits. This way, you’ll continue contributing to your HSA and can get full Medicare benefits later on.
Keep in mind that Medicare isn’t the same for everyone. Enrollees need to evaluate their individual health and lifestyle needs. Traditional Medicare consists of Part A for hospital care, Part B for doctor visits, Part D for medications, and typically requires a Medicare Supplement (Medigap) policy. There’s also Part C, which is Medicare Advantage, and it’s offered by private insurers and can cover drugs, hospital care, and even extras like vision and dental care, though there are sometimes stricter rules on treatment approvals and provider networks.
For your situation, there’s no pressing need to delay enrolling in Part A, apart from the HSA contribution issue while you’re still working. Generally, Part A comes without premiums and serves as a backup. You should wait to register for Part B until you no longer qualify for your employer’s coverage, ensuring you do so during the special enrollment period to dodge penalties. You will stop HSA contributions, but the existing funds in your account remain intact.
Using an HSA has tax benefits—it’s tax-deductible, grows tax-free, and withdrawals for qualified medical expenses are also tax-free. Plus, you can use those funds now or save them for Medicare premiums, long-term care, or out-of-pocket expenses during retirement. If you’re planning to enroll in Medicare, it’s wise to stop HSA contributions six months before your Part A start date. If you’ve built up a substantial HSA, additional contributions may not really change much, especially if you tend to save rather than spend those funds.
Need a financial advisor?
A financial planner who understands retirement planning and healthcare can help clarify Medicare decisions alongside broader financial matters. However, if Medicare is your only concern, hiring one might not be necessary. Instead, you could seek unbiased guidance from state medical assistance programs which offer one-on-one Medicare advice.
Before considering a paid advisor, you might want to first consult a SHIP (State Health Insurance Assistance Program) counselor or a Medicare-savvy advisor who can assist you for free, suggests Philip Battin, president and CEO of Ambassador Wealth Management. To navigate this smoothly, Orestis recommends getting in touch with a licensed insurance agent specializing in Medicare plans—these professionals can provide invaluable, no-cost advice.
