A lot of people specifically wait until age 65 to retire because that's when Medicare eligibility begins. In fact, you can enroll in Medicare up to three months ahead of the month you turn 65.
If you're turning 65 this year, or you were 65 before 2026 started, you may be considering enrolling in Medicare before Dec. 31. But should you? Ask yourself these key questions to find out.
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1. Do you still have group healthcare through your job?
Although most Medicare enrollees do not pay a monthly premium for Part A, which covers hospital care, Part B charges a monthly premium. So if you're still working at age 65, then it doesn't necessarily make sense to enroll in Medicare. You may find that your employer's health plan is superior to Medicare in terms of cost and quality.
That said, you should know that if you don't have creditable health coverage during the time of your initial Medicare enrollment window, you could risk penalties for signing up late. So it's important to make sure you're exempt from a late enrollment penalty based on your coverage. Generally, that applies if you're on a group health plan with 20 or more employees.
2. Are you currently contributing to an HSA?
If you're enrolled in a high-deductible health insurance plan, then you may be eligible to contribute to a health savings account, or HSA, in 2026. HSAs allow you to make pre-tax contributions, shielding some of your paycheck from taxes. Plus, HSA funds get to grow tax-free, and withdrawals used for qualifying medical expenses are tax-free as well.
Once you enroll in Medicare, you're no longer able to make HSA contributions. And that could mean losing out on a big tax break. So if you have an HSA, you may want to wait on your Medicare enrollment if you're still covered through a qualifying group health plan.
Remember, HSAs can be a very valuable tool in retirement. Not only can you use the money to cover healthcare expenses, but once you turn 65, HSAs work like a traditional IRA or 401(k) in that non-medical withdrawals aren't penalized and are simply subject to taxes. So all told, you get a lot of flexibility with your account, which is why it could pay to keep funding one as long as you can.
Even though many people opt to enroll in Medicare once they turn 65, it's not a given that that's a smart move. If you don't need Medicare right away, it could make sense to delay your enrollment as long as you won't face a penalty for doing so.
