Medicare Planning Strategies With a Financial Advisor

The Centers for Medicare and Medicaid Services (CMS) sets premiums, deductibles, and income-related surcharge brackets annually. Below are the figures that matter most for retirement income planning strategies.

$202.90
Standard Part B Monthly Premium

$283
Part B Annual Deductible

$38.99
Part D Base Beneficiary Premium

Oct 15
Open Enrollment Begins (through Dec 7)

Source: CMS, released November 14, 2025. As of August 2026.

Understanding when to enroll in Medicare can help you avoid late-enrollment penalties and coverage gaps. Below are the key enrollment periods that affect most pre-retirees.

Initial Enrollment Period (IEP)

Lasts seven months: the three months before your 65th birthday, the month of your birthday, and three months after. Enrolling during the first three months may allow coverage to begin the month you turn 65. Coverage start dates depend on when enrollment occurs within this window.

Medicare Open Enrollment (October 15 to December 7)

Each year from October 15 through December 7, you can join, switch, or drop Medicare Advantage and Part D plans. Changes generally take effect January 1 of the following year, if the plan receives the request by December 7. For 2026, this period runs October 15 through December 7, 2026, for coverage changes effective in 2027.

General Enrollment Period (January 1 to March 31)

If you missed your Initial Enrollment Period and do not qualify for a Special Enrollment Period, you can enroll in Part A and Part B between January 1 and March 31 each year. Coverage generally begins the month after enrollment, and late-enrollment penalties may apply.

Special Enrollment Periods (SEPs)

Available if you or your spouse are covered under a group health plan based on current employment. SEPs allow you to delay Part B enrollment without penalty. When employment or coverage ends, you generally have an eight-month window to enroll. Eligibility depends on individual circumstances.

Source: Medicare.gov and Medicare.gov Open Enrollment. As of August 2026.

Medicare does not exist in isolation from the rest of your retirement plan. The income you draw from taxable accounts, traditional IRAs, pensions, and Social Security all flow through your tax return, which in turn determines your IRMAA surcharge two years later. Our team coordinates these moving parts so that Medicare decisions are made with full awareness of their tax and cash-flow implications.

For example, a pre-retiree who delays Social Security until age 70 may need to draw more from taxable accounts in the interim, potentially increasing MAGI and triggering IRMAA surcharges. Similarly, a Roth conversion that reduces future RMDs and long-term tax burden may temporarily increase Medicare premiums. Understanding these trade-offs is essential to making informed decisions.

What We Coordinate

• Social Security claiming timing and its effect on taxable income
• Retirement account withdrawal sequencing to manage MAGI
• Roth conversion timing relative to IRMAA brackets
• Pension income and its contribution to modified AGI
• Capital gains harvesting and its IRMAA implications
• Annual review of plan changes during Open Enrollment

Common questions from pre-retirees and retirees in Connecticut, Rhode Island, New York, New Jersey, Massachusetts, New Hampshire, and Vermont.

What Is an IRMAA Surcharge?

IRMAA is an income-related surcharge that CMS adds to standard Medicare Part B and Part D premiums for beneficiaries whose modified adjusted gross income exceeds set thresholds. For 2026, an individual with 2024 MAGI above $109,000, or a married couple filing jointly with MAGI above $218,000, may be subject to IRMAA. The surcharge amount increases in tiers as income rises. Source: CMS, released November 14, 2025.

How Do I Avoid or Reduce Medicare's IRMAA Premium Surcharge?

IRMAA is determined by your MAGI from two years prior, so reducing taxable income in a given year may lower your surcharge two years later. Strategies that may help include spreading large withdrawals over multiple years, timing Roth conversions carefully, and utilizing qualified accounts. However, each strategy involves trade-offs, and results depend on individual tax circumstances. A financial advisor can help model different scenarios.

Do Husband and Wife Both Pay IRMAA Separately?

Yes. IRMAA is assessed separately for each spouse who is a Medicare beneficiary, but the income threshold is based on your combined MAGI if you file jointly. Both spouses could face surcharges if your joint income exceeds the threshold, and each spouse's surcharge is calculated based on your shared tax return. If you file separately, different thresholds apply.

Does the IRMAA Surcharge Ever Go Away?

IRMAA is reassessed annually based on your most recent available tax return. If your income drops below the threshold in a future year, the surcharge may be reduced or eliminated for the corresponding Medicare year. You can also request a reconsideration from Social Security if you experienced a life-changing event such as retirement, divorce, or death of a spouse that reduced your income.

What Is the Biggest Mistake Seniors Make When Enrolling in Medicare?

One of the most common and costly mistakes is failing to enroll in Part B during the Initial Enrollment Period when not covered by a qualifying employer group health plan. This can trigger a permanent late-enrollment penalty of 10% for each 12-month period of delay. Another frequent error is not understanding how retirement income affects IRMAA, leading to unexpected premium surcharges.

What Happens if You Choose Not to Sign Up for Medicare at 65?

If you do not enroll in Part B during your IEP and are not covered by a qualifying employer group health plan, late-enrollment penalties may apply. For Part B, the penalty is 10% of the standard premium for each full 12-month period you were eligible but did not enroll. For Part D, the penalty is 1% of the national base beneficiary premium for each month without creditable coverage. Both penalties typically persist for as long as you have Medicare.

Is It Better to Have Original Medicare or a Medicare Advantage Plan?

There is no single answer; the right choice depends on your healthcare needs, preferred providers, prescription drug usage, budget, and travel patterns. Original Medicare offers broader provider access nationwide, while Medicare Advantage plans may offer additional benefits such as dental and vision coverage but typically use provider networks. A financial advisor can help you evaluate how each option fits within your retirement income plan, but we do not recommend specific Medicare plans. Plan selection is an individual decision.