Healthcare is one of the biggest and least predictable expenses in retirement, and Medicare is at the center of it. When you enroll and which coverage you choose affect your monthly budget, your out-of-pocket risk, and ultimately, how long your savings last.
Whether you're approaching 65 or already on Medicare, here are answers to three of the most common questions our clients ask, updated for 2027.
1. When should I sign up?
Most people first become eligible for Medicare at 65. Your Initial Enrollment Period is a seven-month window: the three months before your birthday month, your birthday month, and the three months after.
Here's something many people don't realize: even if you aren't collecting Social Security yet, you may still need to sign up for Medicare Part B at 65. If you don't, and you don't have other qualifying coverage, you could pay a late enrollment penalty of 10% for every full year you went without it. That penalty lasts as long as you have Part B, and your coverage could be delayed.
The big question is whether you're covered by a group health plan through current employment, either your own or your spouse's.
• No employer coverage? Sign up during your Initial Enrollment Period.
• Still covered through active work? You may be able to delay Part B without penalty. When that job or coverage ends, whichever comes first, you get an eight-month Special Enrollment Period to sign up.
• Small employer? If the employer has fewer than 20 employees, Medicare usually becomes your primary insurance at 65, so you'll likely need Part B right away.
One important catch: COBRA and retiree coverage don't count as coverage from current employment. Relying on them to delay Part B is one of the most common and costly mistakes we see. Before you decide, check with your HR department or talk with us.
2. What are my Medicare options?
Medicare has four parts, plus supplemental coverage. Here's a simple breakdown.
Part A — Hospital insurance. Covers inpatient hospital care, skilled nursing facility care, hospice and some home health care. Most people pay no premium for Part A if they or their spouse worked and paid Medicare taxes for at least 10 years.
Part B — Medical insurance. Covers doctor visits, outpatient care, lab work, preventive services and some medical equipment. Most people pay a standard monthly premium, which is projected at about $209.50 for 2027. Higher-income households pay more.
Part C — Medicare Advantage. These are plans offered by private insurance companies approved by Medicare. They cover everything Parts A and B cover, and most include prescription drug coverage. Many also add extras like dental, vision and hearing benefits. Premiums are often low, and some are $0 beyond your Part B premium. The trade-off is that most plans use provider networks and charge copays as you use care, up to an annual out-of-pocket limit.
Part D — Prescription drug coverage. Part D plans help pay for your medications, usually with a premium, a deductible and copays based on drug “tiers.” For 2027, the most you'll pay out of pocket for covered drugs is $2,400, up from $2,100 in 2026, and the maximum deductible rises to $700. Every plan covers a different list of drugs at different prices, so it's important to check that your medications are covered.
Medicare Supplement (Medigap). If you stay with Original Medicare (Parts A and B), a Medicare Supplement plan helps pay costs Medicare doesn't, such as deductibles and the 20% coinsurance. Supplements let you see any provider who accepts Medicare, but they don't include drug coverage, so most people pair one with a Part D plan. In New York, you can apply for a Medicare Supplement any time of year without being turned down for health reasons, which isn't the case in most states.
3. What if I'm in the wrong plan?
You're not stuck. Your needs, your medications and the plans themselves change every year, so it's smart to review your coverage annually, even if you were happy with it last year.
• Annual Enrollment Period: October 15 – December 7.You can switch Medicare Advantage plans, change Part D plans, or move between Original Medicare and Medicare Advantage. Changes take effect January 1.
• Medicare Advantage Open Enrollment Period: January 1 – March 31. If you're in an Advantage plan, you can make one change, either to a different Advantage plan or back to Original Medicare.
This year's review is especially important. Some Medicare Advantage plans are leaving certain areas or trimming extra benefits like dental for 2027. Part D costs are shifting, and new Medicare-negotiated prices take effect January 1 for 15 more drugs, including Ozempic, Wegovy and Rybelsus. Check the “Annual Notice of Change” letter from your plan to see what's different for you.
Get one-on-one Medicare help
Medicare choices are an important part of your overall retirement plan. That's why we work alongside our sister company, Complete Medicare Services, whose licensed advisors meet with you one-on-one to review your doctors, prescriptions and budget and compare your options. There's never a fee for a consultation.
The 2027 Annual Enrollment Period ends December 7. Schedule your free Medicare review with Complete Medicare Services or call 716-490-MEDS (716-490-6337).
And if you'd like to talk about how healthcare costs fit into your broader retirement income plan, contact The Legend Group anytime.
Not connected with or endorsed by the United States government or the federal Medicare program.