New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

Sears Holdings Employees: Preparing for the 2026 Social Security COLA Increase

Healthcare Provider Update: Healthcare Provider for Sears Holdings Sears Holdings typically provides healthcare benefits to its employees through various insurance plans, often with national insurers such as Aetna, UnitedHealthcare, or Anthem Blue Cross Blue Shield being among the health carriers they have partnered with. The specific providers can vary by location and employee selection during open enrollment periods. Potential Healthcare Cost Increases in 2026 As we progress into 2026, the healthcare landscape is expected to face significant challenges, particularly for employees of Sears Holdings. Forecasts indicate steep premium hikes, with some states imposing increases of over 60%, largely influenced by rising medical costs and the potential expiration of enhanced ACA premium subsidies. The Kaiser Family Foundation highlights that without congressional intervention, millions of marketplace enrollees could see their out-of-pocket costs surge by more than 75%. This convergence of factors threatens to impose a substantial financial burden on both individuals and employers, necessitating proactive strategies to mitigate rising expenses. Click here to learn more

'With the 2026 Social Security COLA set to increase income for many Sears Holdings employees in retirement, thoughtful coordination of benefits and withdrawals is essential, as rising income can also elevate tax exposure.' —Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'While the Social Security COLA boost may offer added income for Sears Holdings employees entering retirement, it’s important to plan carefully, as higher benefits can also raise taxable income over time.'—Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How the 2026 Social Security cost-of-living adjustment (COLA) impacts Sears Holdings retirees.
Tax implications of higher Social Security benefits and ways to manage them.
Timing strategies for Social Security benefits and available deductions for retirees.

What Sears Holdings Retirees Need to Know About Social Security COLA 2026

The Social Security cost-of-living adjustment (COLA) for 2026 is set at 2.8%, slightly higher than the previous year’s 2.5% increase. ¹ This annual COLA, announced by the Social Security Administration (SSA) in October and applied to January benefits, helps retirees maintain purchasing power during inflationary periods. For Sears Holdings employees nearing or in retirement, this adjustment can play a key role in income planning.

According to the Bureau of Labor Statistics, the Consumer Price Index for Urban Wage Earners and Clerical Workers (CPI-W)—which determines COLA—increased 3% over the 12 months ending September 2025. ²

While this is lower than the 8.7% increase in 2023, ³ it may still offer meaningful relief to Sears Holdings retirees experiencing higher living expenses.

How Higher Benefits Could Affect Taxes

As Social Security benefits rise, your combined (or “provisional”) income may increase, which can cause a greater portion of your benefits to be taxed. Combined income includes wages, pensions, interest, dividends, taxable withdrawals from traditional 401(k)s or IRAs, non-taxable interest, and half of your Social Security benefits.

For single filers with income below $25,000 and joint filers below $32,000, Social Security benefits are not taxed. Between $25,000 and $34,000 for single filers and $32,000 and $44,000 for joint filers, up to 50% of benefits may be taxable. Income above those ranges can result in up to 85% of benefits being taxable. ³ These income thresholds are not adjusted for inflation, which means Sears Holdings retirees may experience increased taxation over time as income rises.

Withdrawals from traditional Sears Holdings retirement plans, such as 401(k)s and IRAs, are treated as ordinary income and can increase the taxable portion of Social Security benefits. Thoughtful timing of withdrawals may help manage tax exposure.

Strategies to Manage Tax Impact

If rising taxes are a concern, the following strategies may help:

Balance withdrawals across account types. Coordinating distributions from tax-deferred, taxable, and Roth accounts may help you meet required minimum distribution (RMD) rules while managing your tax bracket.
Use taxable accounts strategically. Only capital gains—not your initial investment—are taxable.
Consider tax-free withdrawals. Qualified distributions from Roth IRAs, Roth 401(k)s, or Health Savings Accounts (HSAs) are not included in taxable income and do not affect Social Security taxation.

New Senior Tax Deduction: 2025–2028

Beginning in 2025, a new senior deduction of $6,000 per person ($12,000 for joint filers) will be available to taxpayers age 65 and older. This deduction phases out at $75,000 adjusted gross income (AGI) for single filers and $150,000 for joint filers.

This deduction is in addition to the age-65+ standard deduction increase of $2,000 for single filers and $1,600 per eligible spouse for joint filers in 2025. Sears Holdings retirees may wish to include this in long-term tax planning.

Timing Your Social Security Benefits

Delaying Social Security until full retirement age (67) or up to age 70 generally results in higher lifetime benefits. Benefits increase by about 8% for each year you delay claiming between your full retirement age and age 70.

For Sears Holdings retirees, delaying benefits may provide additional flexibility in coordinating income from pensions, savings, or retiree medical accounts.

Social Security provides inflation-adjusted income for life, which may contribute to financial stability when aligned with corporate retirement benefits.

Keep the Big Picture in Mind

While the 2026 COLA helps counter rising costs, it can also raise taxable income for some retirees. Thoughtful planning around withdrawals, deductions, and timing of benefits can help manage long-term taxes. Because tax laws are complex, developing a multi-year strategy with a financial advisor is recommended.

The Retirement Group can help Sears Holdings employees explore Social Security strategies, tax-focused withdrawal planning, and retirement income coordination. For more information, call The Retirement Group at (800) 900-5867 .

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Sources:

1. Social Security Administration. Social Security Announces 2.8 Percent Benefit Increase for 2026 . U.S. Government, 24 Oct. 2025, https://www.ssa.gov/news/en/press/releases/2025-10-24.html .

2. Bureau of Labor Statistics. ' Consumer Price Index Summary ,' September 2025.

3. Markowitz, Andy. “Why Social Security COLAs Can Increase Your Taxes.” AARP , 6 Feb. 2024, updated 10 Feb. 2025, https://www.aarp.org/social-security/benefits-taxes-cola/ .

How does the Sears Holdings Pension Plan differentiate between normal retirement, early retirement, and late retirement options for Kmart participants? In what ways do these options influence the retirement planning process for employees of Sears Holdings, and what specific considerations should Kmart employees be aware of when choosing one of these retirement paths, particularly in relation to their vested status?

Differentiation of Retirement Options: The Sears Holdings Pension Plan offers distinct options for normal, early, and late retirement. Normal retirement is available at age 65 or after five years of plan participation, whichever is later. Early retirement can be taken from age 55 but before 65, provided the employee is vested, with benefits subject to actuarial reduction unless certain conditions are met (like having at least 90 points, which is a sum of age and years of credited service). Late retirement pertains to any retirement after the normal retirement age, with pensions recalculated to reflect the delay in benefit commencement.

Considering the frozen status of the Sears Holdings Pension Plan, how does this impact the benefits eligibility for Kmart employees, and what implications does it have for their retirement savings strategies? In what ways should current employees factor in this frozen status when evaluating their overall retirement readiness and potential alternatives outside of the company plan?

Impact of Frozen Status: The freezing of the Sears Holdings Pension Plan on January 31, 1996, means that there have been no new accruals of benefits or participants since that date. For Kmart employees, this impacts their benefits eligibility by capping the pension benefits at levels earned up to the freeze date. Employees need to consider this stagnation in benefits when planning for retirement, potentially seeking additional retirement savings avenues to bridge any shortfall.

What are the essential calculations involved in determining the retirement benefits under the Sears Holdings Pension Plan for Kmart employees? Specifically, how do the Career Average Pay and Final Average Pay formulas come into play, and what factors should employees consider when estimating their future retirement payouts?

Essential Calculations for Retirement Benefits: Pension benefits for Kmart employees under the Sears Holdings Pension Plan are calculated using either the Career Average Pay or the Final Average Pay formulas. These calculations take into account an employee's years of credited service and compensation up to the freeze date. Factors like estimated Social Security benefits and specific formulas (such as a deduction based on Social Security benefits under the Final Average Pay formula) play crucial roles in determining the final pension payout.

How can Sears Holdings employees best navigate the process of applying for benefits under the Pension Plan? What specific steps should participants take to ensure their applications are processed correctly, and what important deadlines should they be aware of to avoid any negative consequences on their retirement benefits?

Navigating the Benefits Application Process: To apply for pension benefits, employees must submit a formal application, ideally 30 to 90 days before the intended commencement date. It is crucial to ensure all personal information, including marital status and spouse details, is up-to-date to avoid delays or inaccuracies in benefit processing. Missing application deadlines can lead to postponed benefit payments or unwanted default options.

In what situations can Kmart employees expect to receive a Deferred Vested Pension, and how is the calculation for this pension affected by their previous employment and vesting service? Employees should be aware of the important factors influencing their eligibility and the steps necessary to maintain their retirement benefits after leaving the company.

Eligibility and Calculation for Deferred Vested Pension: A Deferred Vested Pension is available to employees who leave the company after becoming vested but prior to qualifying for retirement. The calculation mirrors that of a normal retirement pension, with possible early commencement reductions. Understanding the timing of benefit commencement and the potential reductions for early start is vital for planning.

How does the Sears Holdings Pension Plan address tax considerations for employees receiving both monthly payments and lump sum payments upon retirement? What tax implications should Kmart participants be aware of, particularly in relation to IRS rules for distributions and potential penalties for early withdrawal?

Tax Implications of Pension Receipt: Pension payments, whether monthly or lump sum, are subject to federal taxes. Monthly benefits are taxed as ordinary income, while lump sums might be eligible for special tax treatments or rollover options to defer taxes. It’s important for Kmart employees to consider these implications and possibly consult with a tax advisor to optimize tax liability.

What are the rights and protections afforded to Kmart participants under the Employee Retirement Income Security Act (ERISA) as they navigate their retirement benefits with the Sears Holdings Pension Plan? How can employees leverage these rights to ensure they are receiving all the benefits to which they are entitled?

ERISA Rights and Protections: Under ERISA, Kmart employees are entitled to certain rights including the ability to appeal denied benefits, access to plan information, and assurances of fair and equitable treatment of their benefits. Leveraging these protections ensures that employees receive all due benefits.

What steps should Kmart employees take to update their personal information to ensure they continue receiving their benefits without interruption, especially in the context of missing participants or uncashed checks? What resources and contacts at Sears Holdings are available to assist with these updates?

Updating Personal Information: Maintaining accurate personal information with the pension plan is crucial for uninterrupted benefit payments. Employees should promptly update changes such as address, marital status, or beneficiaries to prevent issues with benefit distributions or lost checks.

How does the process of transferring between affiliated employers impact pension benefits for Kmart employees under the Sears Holdings Pension Plan? What considerations should be taken into account concerning Credited Service and Vesting Service during such transfers, and how can employees ensure they do not lose any entitled benefits?

Impact of Transfers Between Affiliated Employers: Transferring between Sears Holdings’ affiliated employers can affect pension benefits differently depending on whether the employer participates in the pension plan. It's essential to understand how such transfers impact credited and vesting service accruals.

For Kmart employees seeking more information about their benefits under the Sears Holdings Pension Plan, what is the best way to contact company representatives? How can they effectively communicate their questions or concerns to ensure they receive accurate and timely information regarding their retirement benefits?

Contacting Plan Representatives: Kmart employees seeking clarity on their pension benefits should contact the Sears Holdings Pension Service Center. Effective communication, including prepared questions and necessary documentation, will aid in obtaining accurate and comprehensive information.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Sears Holdings Corporation's pension plans were taken over by the Pension Benefit Guaranty Corporation (PBGC) following the company's bankruptcy. The two defined benefit pension plans have been frozen since 2005, meaning no new benefit accruals are added. The plans are underfunded by approximately $1.4 billion, with PBGC assuming responsibility to ensure pension payments continue. These plans cover about 90,000 participants who worked for Sears, Roebuck and Co., and Kmart Corporation. Despite the underfunding, PBGC is expected to cover the vast majority of pension benefits owed under these plans. Participants can manage their benefits and verify information through PBGC's online platform or service center.

Bankruptcy and Store Closures: Sears Holdings emerged from bankruptcy with significant store closures, reducing from nearly 700 stores to less than 25. The company has been liquidating its remaining assets and recently announced more store closures in 2024. The focus is on resolving bankruptcy-related issues and managing the liquidation process effectively (Sources: The Layoff, Yahoo Finance).

Sears Holdings offered both RSUs and stock options before its bankruptcy. RSUs vested over time, providing shares, while stock options allowed employees to buy shares at a fixed price.

Sears Holdings, now part of Transformco, has faced numerous challenges in recent years, impacting its ability to provide comprehensive employee healthcare benefits. The strategic transformations initiated since 2017 aimed to improve operational performance and liquidity, which included measures such as obtaining additional loan proceeds and real estate sales. However, the company's financial struggles and store closures have also led to significant changes in employee benefits, including healthcare. As part of its efforts to stabilize and restructure, Sears has focused on reducing outstanding debt and pension obligations, contributing almost $4 billion to its pension plan since 2005 due to prolonged low interest rates. In 2023, Transformco continued to navigate its financial challenges, which have influenced its healthcare benefits offerings. The company has aimed to maintain basic healthcare coverage for its employees despite ongoing restructuring efforts. This includes providing access to medical, dental, and vision plans, although the specifics of these benefits and any enhancements over the past years have been less prominently highlighted compared to the broader financial strategies and operational changes. The focus on financial stability and cost reduction remains critical for Transformco as it seeks to ensure the viability of its employee benefits programs amid economic uncertainties.

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For more information you can reach the plan administrator for Sears Holdings at 3333 beverly road Hoffman Estates, IL 60179; or by calling them at 1-800-697-3277.

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