Health Insurance After Early Retirement: Options for the Gap Before Medicare

For people who leave the workforce before age 65, one of the more immediate practical questions is what to do about health insurance. Medicare eligibility begins at 65 for most people, which means anyone who retires earlier faces a coverage gap. Depending on when someone retires, that gap could be a matter of months or close to a decade.

There is no universal answer. The right approach depends on a household's specific circumstances: the length of the gap, whether a spouse is still working, what a former employer offers, how retirement income is structured, and how much flexibility in plan design matters. Some people use a single option for the entire gap; others sequence two or three approaches as circumstances change. Short-term health plans are another category some people consider, though federal rules governing their duration are in active flux as of this writing; anyone evaluating them should verify current state and federal regulations before making a decision.

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Published: August 28, 2026

The opinions shared in this article are solely those of the advisors at Rockford Financial Planning. All information within is reflective of the article's publishing date.

This content is not intended as investment, legal, or tax advice. Historical performance and economic data are for informational purposes only and do not predict future results. Consult with a qualified legal or financial professional before acting on any financial information found here.


COBRA Continuation Coverage

The Consolidated Omnibus Budget Reconciliation Act (COBRA) allows most people leaving employer-sponsored group health coverage to continue that same coverage for up to 18 months after separation. For someone retiring at 63 or 64, this can serve as a straightforward bridge to Medicare eligibility.

A few things worth understanding:

  • Coverage is identical to what was in place through the employer plan, which can be an advantage for people who are mid-treatment or have established provider and specialist relationships they want to preserve
  • The cost increases significantly because the employer's contribution goes away; the former employee becomes responsible for the full premium plus an administrative fee, which is typically capped at 2% of the premium
  • The 18-month window is fixed, so timing matters considerably; someone retiring at 62 would exhaust COBRA well before Medicare eligibility at 65

For someone with a gap of 18 months or less, COBRA is one of the more straightforward options to assess. Whether it represents the right approach depends on cost, health status, and what other options are available.


Coverage Through a Spouse's or Partner's Employer Plan

If a spouse or domestic partner is still working and has access to employer-sponsored coverage, joining that plan may be among the more cost-effective options to evaluate during the coverage gap, depending on premium costs, network, and plan terms. Employer contributions to premiums do not disappear simply because one partner retires.

A few considerations:

  • Most employer plans allow a non-working spouse to join or remain on the plan regardless of employment status, though plan-specific rules vary
  • Premiums for two people on a group employer plan are often still more affordable than most individual market alternatives
  • This option disappears when the working spouse also retires, so planning for the remaining gap may still be necessary depending on the timing

For households where one partner continues working through the other's early retirement, this option can effectively eliminate the coverage gap entirely, or at least reduce it to a much shorter window.


Retiree Health Benefits from a Former Employer

Some employers, particularly large corporations, public sector organizations, and certain union-affiliated employers, offer continued health benefits to retirees. These benefits are separate from COBRA and are not subject to the 18-month limitation.

Retiree health benefits have become less common over time, but they remain available in certain industries and career paths. People who spent careers in government, education, or large unionized industries may have access to this option.

If retiree health coverage is available, it is generally worth comparing carefully against individual market alternatives. Employer contributions, when present, can make retiree coverage meaningfully more affordable than purchasing a plan independently.


ACA Marketplace Coverage for Early Retirees: Subsidies, MAGI, and Income Strategy

The Affordable Care Act (ACA) Marketplace offers individual health insurance plans to people outside of employer-sponsored coverage. For early retirees, particularly those without access to COBRA, a working spouse's plan, or retiree benefits, it is one of the most commonly used options. For households with income within a specific range, it also offers access to premium subsidies. The rules governing subsidy eligibility changed significantly at the start of 2026.

Losing employer-sponsored coverage at retirement qualifies as a Special Enrollment Period (SEP) triggering event. This typically opens a 60-day window to enroll in a Marketplace plan outside of the standard Open Enrollment period. This is relevant for people who retire mid-year or who need coverage outside the November–January enrollment window.

How subsidies work

ACA Marketplace premium subsidies are calculated based on Modified Adjusted Gross Income (MAGI). MAGI for ACA purposes is calculated as adjusted gross income from your federal tax return, plus any tax-exempt interest income and the non-taxable portion of Social Security benefits. It reflects income as it flows through the tax return, not total wealth or account balances. This distinction matters significantly for people who have accumulated substantial wealth over their careers but retire with relatively modest reportable income in a given year.

A household with $2 million in assets and minimal reportable income may qualify for premium subsidies, provided their MAGI falls below the income ceiling discussed below. A household with $400,000 in annual W-2 earnings will not, even if they have far less total wealth. The ACA does not see a brokerage account balance, a home's equity, or a cash reserve. It sees only the income that flows onto a tax return in a given year.

One important change took effect for 2026: the enhanced premium tax credits that were in place from 2021 through 2025 expired on December 31, 2025. During those years, subsidy eligibility extended to households at any income level. Under the original ACA rules now back in effect for 2026, subsidies are available only to households with MAGI between 100% and 400% of the federal poverty level (approximately $15,650 to $62,600 for a single person). This is a hard cutoff, not a phase-out: a household earning $62,600 qualifies for the minimum subsidy, while a household earning $62,601 receives no federal premium assistance at all. Households with MAGI above that ceiling receive no federal premium subsidy regardless of how income is structured. The sequencing strategies discussed below apply to households that expect to fall within the eligible range.

The cost environment for 2026 Marketplace coverage changed substantially when the enhanced credits expired. According to KFF, average net monthly premiums among Marketplace consumers rose 58%, climbing from $113 to $178 per month compared to 2025. For subsidized enrollees who kept the same plan, premium payments increased by an estimated 114% on average. At the same time, the average deductible on Marketplace plans rose by more than $1,000, partly because many enrollees shifted from silver to lower-premium bronze plans to manage monthly costs. These figures vary by income, household size, location, and plan type, but they illustrate the materially different cost baseline early retirees face when shopping for Marketplace coverage in 2026.

What the ACA counts and does not count as income

Not all financial activity generates MAGI, and this is where income sequencing becomes particularly relevant for early retirees using the Marketplace.

Income that counts toward ACA MAGI
  • Withdrawals from Traditional IRA or 401(k) accounts, counted dollar for dollar
  • Capital gains from selling appreciated positions in taxable brokerage accounts
  • Dividends from investments in taxable accounts
  • Social Security benefits, once you begin receiving them
  • Tax-exempt municipal bond interest, which is added back into ACA MAGI even though it is exempt from federal income tax
Income that does not count toward ACA MAGI
  • The return of original investment basis from a taxable brokerage account (only the gain portion is income)
  • Proceeds from loans, including home equity lines of credit or loans against cash value life insurance policies
  • Qualified Roth IRA and Roth 401(k) distributions


Approaches to managing MAGI

The strategies below apply to households whose projected retirement income falls within the 100% to 400% FPL range for their household size (approximately $15,650 to $62,600 for a single person in 2026), or can be sequenced to stay within it. For households with income that consistently exceeds that ceiling regardless of withdrawal sequencing, ACA premium subsidies are not available, and coverage cost planning must account for the full unsubsidized premium.

For early retirees using the ACA Marketplace, income sequencing strategies (choosing which accounts to draw from and when) can affect both subsidy eligibility and the net cost of coverage.

Drawing from Roth accounts

Qualified Roth IRA and Roth 401(k) distributions do not factor into the ACA MAGI calculation. Spending from Roth balances in a given year leaves MAGI exactly where it was before the withdrawal.

Spending down cash and liquid non-retirement assets

Cash savings and liquid non-retirement assets generate no MAGI when spent. Drawing down cash reserves before tapping income-generating accounts may help keep MAGI lower in a given year.

Managing capital gains with intention

In a taxable brokerage account, only the portion of proceeds above the original cost basis counts as income. Selecting which positions to sell, and in what amounts, may allow a retiree to fund spending needs while limiting the income recognized in a given year. Tax-loss harvesting, where applicable, can also offset recognized gains.

Tax-loss harvesting: This strategy involves selling positions held at a loss to reduce the net capital gains income recognized in a given year. The mechanics and timing of tax-loss harvesting can be nuanced, and a tax professional or financial advisor can help determine whether and how it applies to a given portfolio.

Timing Social Security if flexibility exists

Social Security benefits, once begun, count toward ACA MAGI. Delaying the start of benefits through the pre-Medicare years extends the window of favorable subsidy treatment while also increasing the eventual monthly benefit. For retirees in good health with other income sources, delaying through age 70 is an option some people find worth modeling.

Using HSA balances for healthcare costs

Health Savings Accounts allow qualified withdrawals for medical expenses to be taken tax-free. Because these withdrawals generate no taxable income, they do not affect MAGI. Applying accumulated HSA balances toward healthcare costs can therefore help keep MAGI lower while still covering medical expenses. This can be a practical resource for those who built up significant HSA balances during their working years.


A note on over-minimizing MAGI

Managing MAGI for subsidy purposes does not necessarily mean minimizing it as aggressively as possible. Deferring all Traditional IRA withdrawals during the pre-Medicare years may result in a significantly larger Required Minimum Distribution (RMD). RMDs are mandatory annual withdrawals taxed as ordinary income. Under the SECURE 2.0 Act, RMDs begin at age 73 for those born between 1951 and 1959, and at age 75 for those born in 1960 or later. 

A large RMD can push income into higher tax brackets late in retirement. Taking measured withdrawals from Traditional accounts during lower-income years may reduce that future burden, even if doing so reduces ACA subsidy eligibility slightly in those years. Identifying the right balance typically involves running multiple income scenarios rather than following a single rule. For instance, taking $20,000 in Traditional IRA withdrawals annually during the pre-Medicare years may modestly reduce ACA subsidies while meaningfully lowering the projected RMD balance at 73 or 75. A financial planner can model how different withdrawal sequences compare over a 5- to 10-year pre-Medicare window.


Part-Time Work with Benefits

Some people who retire from full-time careers take on part-time or contract roles specifically because those positions include health benefits. Certain large employers extend benefits to part-time employees above a defined weekly-hours threshold.

This approach can combine income, structure, and coverage in a way that appeals to some early retirees. It also has implications for MAGI and ACA subsidy eligibility, since earned income counts toward the MAGI calculation. For someone whose part-time income pushes MAGI above subsidy thresholds, the cost-benefit of the work arrangement relative to the coverage it provides may be worth modeling before committing.


Key Factors in Choosing a Pre-Medicare Coverage Strategy

The options above are not mutually exclusive, and the right combination often changes over the course of a multi-year gap. Someone who retires at 62 might use COBRA for 18 months, then transition to the ACA Marketplace for the remaining years before Medicare. Someone whose spouse works until 64 may have a much shorter and simpler gap to plan for.

Each of these factors shapes not just which options are available, but how they compare in cost and coverage depth.

Length of the gap

The longer the gap, the more the costs compound and the more options matter. A two-year gap and a ten-year gap call for very different planning approaches.

Health status and anticipated medical needs

Coverage depth and continuity tend to matter more for someone managing ongoing conditions or expecting significant healthcare use.

Income sources and structure

How income flows in retirement directly affects ACA subsidy eligibility and the relative value of Marketplace coverage versus other options.

State of residence

ACA Marketplace plan availability and pricing, the rules governing alternative coverage options, and some group plan options vary meaningfully by state.

Whether a spouse is still working

This single factor can simplify the decision significantly. When one partner's employer plan remains available, much of the planning complexity around the gap may be reduced or eliminated.



When to Plan Your Pre-Medicare Health Insurance Coverage Each Year

ACA Open Enrollment typically runs from November 1 through mid-January (January 15 in most federal Marketplace states) for the coming year's coverage. Enrolling by December 15 is necessary to have coverage begin January 1; enrollments completed in January typically result in a February 1 start date (State-based Marketplaces may have different deadlines.) This window aligns naturally with year-end financial planning, but it is also a practical prompt for reviewing the full picture more broadly.

By fall, there is generally a clearer view of the current year's income and a solid basis for projecting the following year. Marketplace premium estimates become available, and decisions about Roth conversions, capital gains realization, and Social Security timing can be made with more complete information. For people using or considering the ACA Marketplace, reviewing income strategy and health insurance strategy together, rather than separately, may lead to more coordinated outcomes.

Even for people who ultimately use a non-Marketplace route, fall is a reasonable time to revisit whether current coverage still makes sense and whether the plan for the remaining gap still holds.


Planning Your Pre-Medicare Income Strategy

For households with significant assets, how income is structured before Medicare begins can have a meaningful effect on both tax liability and healthcare costs. The decisions made during this window tend to interact in ways that benefit from coordinated planning. Speaking with a financial advisor who works with early retirees is one way to model the tradeoffs specific to your situation.

Reach out to our team to start the conversation.


Rockford Financial Planning is a fee-only, fiduciary financial advisory firm based in Wilmington, Delaware, serving clients nationwide. We work with families and small businesses to bring clarity to complicated financial decisions, from retirement and investment planning to coordinating strategies across generations. Meetings are available in person, by phone, or virtually, whatever works best for you.

Read More:

  1. U.S. Department of Labor — Continuation of Health Coverage (COBRA)
    https://www.dol.gov/general/topic/health-plans/cobra
  2. HealthCare.gov — Modified Adjusted Gross Income (MAGI)
    https://www.healthcare.gov/glossary/modified-adjusted-gross-income-magi/
  3. IRS.gov — Roth IRAs
    https://www.irs.gov/retirement-plans/roth-iras
  4. IRS.gov — Retirement topics - Required Minimum Distributions RMDs)
    https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-required-minimum-distributions-rmds
  5. Medicare.gov — When does Medicare coverage start?
    https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
  6. KFF — What We Know So Far About 2026 ACA Marketplace Enrollment, Premiums, and Deductibles
    https://www.kff.org/affordable-care-act/what-we-know-so-far-about-2026-aca-marketplace-enrollment-premiums-and-deductibles/
  7. HealthCare.gov — Special Enrollment Periods
    https://www.healthcare.gov/glossary/special-enrollment-period/
  8. 3. IRS Publication 969 — Health Savings Accounts and Other Tax-Favored Health Plans
    https://www.irs.gov/publications/p969
  9. Social Security Administration — When to Start Receiving Retirement Benefits
    https://www.ssa.gov/pubs/EN-05-10147.pdf