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Questions ยท Work and Social Security

Work and Social Security Medicare questions

These answers cover work, Social Security, employer coverage, and timing questions that can change the Medicare sequence.

Updated August 17, 2026

Which work and social security questions should you start with?

Should I delay Part A if I am still contributing to an HSA?

Yes, you should delay Part A enrollment if you are actively contributing to a Health Savings Account (HSA), because enrolling in Part A makes you ineligible to contribute to an HSA going forward, even retroactively in some cases.

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Do veterans need Medicare, and how do VA benefits work with Medicare?

Veterans can use both VA benefits and Medicare, and they work alongside each other rather than being combined. Neither program pays for care received through the other, so which one you use depends on where you go and what you need.

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Does employer size affect whether I need to take Part B at 65?

Yes, employer size matters a lot. If you work for a company with 20 or more employees, your group health plan is primary and you can usually delay Part B without penalty. With fewer than 20 employees, Medicare pays first and delaying Part B can create serious coverage gaps.

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Is Medicare automatic if I am already receiving Social Security?

Yes, in most cases. If you are already receiving Social Security benefits before you turn 65, you will generally be enrolled in Medicare Parts A and B automatically. Your card will arrive in the mail about three months before your 65th birthday.

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Can Part A be backdated and what does that mean for my HSA?

Yes, Medicare Part A can be backdated up to 6 months when you sign up late. If that happens, your Health Savings Account (HSA) contributions during that backdated period become a problem with the IRS.

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Can I stay on my spouse's employer plan instead of taking Medicare?

Yes, in many cases you can delay Medicare if you're covered by a spouse's active employer plan. But the rules depend on the employer's size, and getting them wrong can trigger permanent penalties.

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What happens if I take COBRA instead of Medicare?

Taking COBRA instead of Medicare when you turn 65 is usually a costly mistake. COBRA is not considered creditable coverage for Medicare purposes, and you could face permanent late enrollment penalties.

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Peter Abilla, Licensed Medicare Insurance Sales Agent, NPN 22265186. Licensed in Alabama, California, Ohio, Pennsylvania, Texas, Utah, New Jersey, New York, North Carolina, Michigan, and Illinois. You reach the same person every call โ€” no transfer queue.