🩺 How to Sign Up for Medicare in 2026 — What Every Tax-Savvy Senior Should Know
Turning 65 soon or planning to retire in the U.S.? Medicare will likely become part of your life — and your tax picture.
While many Americans automatically get coverage, others need to apply, choose between plans, and understand how income affects their monthly premiums.
This guide explains how to sign up for Medicare in 2026, what it costs, and how it interacts with your tax situation under the 2025 tax law.
1️⃣ Automatic vs. Manual Enrollment
Not everyone is automatically signed up for Medicare.
If you already receive Social Security or Railroad Retirement Board (RRB) benefits, you’ll be enrolled automatically in both Part A (Hospital Insurance) and Part B (Medical Insurance) starting the month you turn 65.
Your red-white-blue Medicare card will arrive about three months before your birthday.
But if you haven’t claimed Social Security yet, you must apply manually.
The simplest way is through SSA.gov/medicare/sign-up.
You can also schedule an appointment at your local Social Security office.
Robert K., a 64-year-old restaurant owner in California, postponed claiming Social Security to delay taxes on his benefits.
Because he isn’t receiving retirement income yet, Medicare didn’t enroll him automatically.
He must apply manually during his Initial Enrollment Period to avoid future penalties.
If you have ALS (Lou Gehrig’s disease), you’re automatically enrolled when disability benefits begin.
Those with End-Stage Renal Disease (ESRD) need to apply with the help of their dialysis facility.
2️⃣ When You Can Enroll — and Why Timing Matters
Medicare has strict enrollment windows. Missing them can lead to lifetime premium surcharges.
Understanding these periods is key for anyone planning their retirement or adjusting health coverage.
- Initial Enrollment Period (IEP): a 7-month window — three months before, the month of, and three months after your 65th birthday.
- Special Enrollment Period (SEP): available if you’re still covered by an employer’s group plan when you turn 65.
You can sign up penalty-free within eight months after employment or coverage ends. - General Enrollment Period (GEP): every year from Jan 1 to Mar 31.
Coverage begins the first day of the month after you apply, but late penalties may apply.
Grace L. works for a large tech company with excellent health coverage.
She can delay Medicare Part B until she retires and then enroll under the Special Enrollment Period (SEP) within 8 months of leaving her job — no penalty applies.
But if she relied on COBRA or Marketplace coverage, she’d lose that exemption.
SEP also covers unusual situations — such as losing Medicaid, employer errors, incarceration, or natural disasters that caused you to miss your deadline.
3️⃣ 2025 Premiums and Late-Enrollment Penalties
Medicare premiums vary by income and work history.
Under the 2025 tax rules (used to set 2026 rates), the standard monthly premium for Part B is $185.
Part A is free for most people who paid Medicare taxes for at least 40 quarters (about 10 years).
Mary and Paul S. file jointly with a 2023 income of $240,000.
Because their modified adjusted gross income exceeds $212,000, they owe an IRMAA (Income-Related Monthly Adjustment Amount) surcharge on their Part B premiums.
If their income drops in 2025, they can request a reduction through SSA.gov.
Late-Enrollment Penalties:
– Part A (if not free): 10% surcharge for twice the number of years you delayed enrollment.
– Part B: 10% extra for every 12-month period you were eligible but not enrolled — for life.
In short, delaying Medicare without qualifying coverage is a costly mistake.
Most retirees have their premiums deducted from Social Security payments.
If you don’t receive benefits yet, you can pay online via your Medicare.gov account or set up Medicare Easy Pay.
4️⃣ How Medicare Works with Other Coverage
Many retirees have more than one type of health insurance — for example, through a spouse’s employer or the military.
Medicare coordinates benefits so only one plan pays first (the primary payer) and the other covers what’s left.
| Type of Coverage | Who Pays First? |
|---|---|
| Employer Plan (20 + employees) | Employer plan → Medicare |
| Employer Plan (< 20 employees) | Medicare → Employer plan |
| Retiree Coverage | Medicare first |
| TRICARE (for military families) | TRICARE if active-duty, otherwise Medicare |
| Medicaid | Medicare first, Medicaid secondary |
When you retire or your group coverage ends, update Medicare records promptly by calling 1-800-MEDICARE to avoid billing errors.
5️⃣ Medicare and Your Taxes — HSA, Deductions & IRMAA
Medicare enrollment isn’t just about health care — it can affect your taxes too.
- HSA (Health Savings Account): You can’t contribute to an HSA once you’re enrolled in Medicare.
Because Part A coverage is retroactive up to 6 months, stop HSA deposits at least 6 months before applying to avoid IRS penalties. - Medical Expense Deduction: Part B, Part D, and Medigap premiums are potentially deductible on Schedule A if your total medical expenses exceed 7.5% of AGI.
- Form 1095-B: Proof of health coverage from Medicare. You don’t file it with your return, but keep it for records.
Linda C., a self-employed consultant, deducted her Medicare Part B and D premiums as medical expenses.
Her total expenses exceeded 7.5% of AGI, allowing her to reduce taxable income by $1,200.
While Medicare premiums aren’t “business expenses,” they still offer personal tax benefits when itemized.
Learn more about premium payment rules at Medicare.gov and consult a tax professional to see if your premiums qualify as deductions.
6️⃣ Key Takeaways for Tax-Aware Retirees
- Apply early — ideally 3 months before turning 65 — to avoid coverage gaps and penalties.
- Review your income each year since IRMAA is based on tax returns from 2 years prior.
- Stop HSA contributions before Medicare begins to avoid IRS issues.
- Include Medicare premiums when evaluating medical expense deductions.
- Re-evaluate coverage annually between Oct 15 and Dec 7 — Medicare Open Enrollment.
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