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

Smart Tax Moves for Sears Holdings Employees in 2026—Refunds, Deadlines, and Retirement Planning Opportunities

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

'Sears Holdings employees who take a proactive approach to tax deadlines, identity protection, and retirement account contributions can position themselves for stronger long-term planning conversations.' – Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'Sears Holdings employees who address tax deadlines early, stay alert to identity theft risks, and thoughtfully review retirement contribution limits may gain greater clarity around their long-term financial direction. Aim to integrate these annual tax decisions into a comprehensive retirement planning discussion while consulting a qualified tax professional for personalized guidance.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

Key tax season deadlines and refund statistics Sears Holdings employees should know.
Steps to reduce tax-related identity theft and common filing errors.
Retirement account contribution limits and planning opportunities for 2026.

With tax forms arriving in mailboxes and inboxes, tax season is officially underway for many Sears Holdings employees. Depending on whether you expect a refund or anticipate owing taxes, filing your 2025 return can feel either rewarding or stressful. Starting early may help streamline the process and potentially limit last-minute pressure.

Statistics from the Internal Revenue Service show that the average refund issued during the 2024 filing season was $3,052 . For many individuals, receiving a refund can provide additional cash flow flexibility during the year.

The filing deadline for most individuals’ 2025 federal income tax returns is April 15, 2026 . If you request an extension by that date, you will have until October 15, 2026 , to file your return. Taxes owed, however, are still due by April 15, 2026. An extension allows additional time to submit paperwork, not additional time to remit payment. Taxpayers affected by federally declared disasters may qualify for deadline relief in certain situations.

There are several additional reasons to begin preparing your taxes early.

1. Take Precautions Against Identity Theft

Submitting a tax return early may lower the chance of tax-related identity theft. In these situations, criminals attempt to file fraudulent returns to claim refunds before legitimate filers submit their information. Filing promptly can limit the window for this type of activity.

If you believe your tax account may have been compromised, you should still file a valid return and pay any taxes due. In some cases, the IRS may ask for a paper return along with Form 14039, Identity Theft Affidavit . The IRS generally communicates with taxpayers through mailed notices rather than unsolicited emails, text messages, or social media messages.

2. Correct Errors and Make Adjustments

If you are waiting for tax documents from an employer, financial institution, or other source, it may be helpful to check whether electronic versions are already available. Accessing documentation earlier allows more time to review information and address potential inaccuracies.

Common tax filing mistakes include mathematical errors, missing income, overlooked credits, and incorrect reporting of investment transactions.

For example, Form 1099-B reports proceeds from investment sales used to calculate capital gains and losses. If total capital losses exceed gains, up to $3,000 may be deducted against ordinary income ( $1,500 if married filing separately ). Unused losses may be carried forward to future tax years.

3. Evaluate Planning Opportunities for 2026 and Beyond

The start of the year is often a practical time to review tax-related decisions that may affect upcoming filings.

You may consider adjusting tax withholding through your payroll department if your current withholding does not match your anticipated tax situation. Early planning may also help clarify contribution decisions for tax-advantaged accounts before the April 15, 2026 deadline.

IRA Contributions

For the 2025 tax year , the contribution limit for both traditional and Roth IRAs is $7,000 , with a higher limit of $8,000 for individuals age 50 or older. For 2026 , the limit increases to $7,500 , with a catch-up amount bringing the total to $8,600 for eligible individuals age 50 and older.

Traditional IRA contributions may lower taxable income for individuals who meet eligibility requirements. A nonworking spouse may also contribute to an IRA if the couple files jointly and has sufficient earned income.

HSA Contributions

For 2025 , Health Savings Account contribution limits are $4,300 for self-only coverage and $8,550 for family coverage, with an additional $1,000 catch-up contribution for individuals age 55 and older.

For 2026 , limits increase to $4,400 for self-only coverage and $8,750 for family coverage. Contributions for the 2025 tax year may generally be made until April 15, 2026.

SEP IRAs and Other Plans

Independent contractors and freelancers—including Sears Holdings employees with consulting or side income—may establish a SEP IRA . For 2025 , contributions are limited to the lesser of $70,000 or 25% of eligible compensation . In 2026 , the maximum contribution increases to $72,000 .

Other retirement plan options for self-employed individuals include SIMPLE IRAs, Solo 401(k) plans, and pooled employer plans (PEPs).

4. Reduce Last-Minute Surprises

Waiting until the final days of the filing season can add unnecessary stress, particularly if taxes are owed. Filing an extension does not postpone payment obligations, and outstanding balances may lead to interest and penalties.

This may be especially relevant for individuals with self-employment or consulting income, who are typically required to make quarterly estimated tax payments. If estimated payments were missed, additional preparation may be required before filing.

5. Finish Early and Stay Organized

Tax preparation is often considered one of the year’s more time-intensive financial responsibilities. Beginning early and maintaining organized records throughout the year can make the process more manageable. Digital storage, consistent documentation practices, and organized filing systems can simplify future tax seasons.

Completing a return early may also provide a clearer view of your overall financial position, which can support broader retirement and income planning discussions.

Organizing Beyond Tax Season

Tax filing is only one element of a broader retirement strategy. Decisions related to IRA contributions, SEP IRAs, HSAs, and other retirement accounts can influence long-term financial outcomes.

Depending on your individual circumstances, The Retirement Group can help review retirement planning considerations aligned with your employment and benefit structure. You can speak with a representative by calling (800) 900-5867 to discuss your retirement planning options.

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Sources:

1. Consumer Financial Protection Bureau. “Guide to Filing Your Taxes in 2026.” Consumer Financial Protection Bureau , https://www.consumerfinance.gov/consumer-tools/guide-to-filing-your-taxes/ . Accessed 6 Feb. 2026.

2. Fidelity. “HSA Contribution Limits and Eligibility Rules for 2025 and 2026.” Fidelity Learn , 26 Aug. 2025, https://www.fidelity.com/learning-center/smart-money/hsa-contribution-limits . Accessed 6 Feb. 2026.

3. Gusto Editors. “401(k) and IRA Contribution Limits in 2026: What’s New This Year.” Gusto , 23 Jan. 2026, https://gusto.com/resources/401k-ira-contribution-limits-2026 . Accessed 6 Feb. 2026.

4. Internal Revenue Service. “Filing Season Statistics for Week Ending Oct. 17, 2025.” IRS , 24 Oct. 2025, https://www.irs.gov/newsroom/filing-season-statistics-for-week-ending-oct-17-2025 . Accessed 6 Feb. 2026.

5. “When Are Taxes Due? Tax Deadlines for 2025–2026.” TurboTax Tax Tips & Videos , Intuit, https://turbotax.intuit.com/tax-tips/tax-planning-and-checklists/important-tax-deadlines-dates/L7Rn92V1d . Accessed 6 Feb. 2026.

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.

https://www.pbgc.gov/sites/default/files/documents/sears-holdings-summary-plan-description.pdf - Page 5, https://88sears.com/documents/pension-plan-2022.pdf - Page 12, https://88sears.com/documents/pension-plan-2023.pdf - Page 15, https://88sears.com/documents/pension-plan-2024.pdf - Page 8, https://www.consultrms.com/documents/sep-2022.pdf - Page 22, https://www.revenue.alabama.gov/documents/defined-benefit-plan.pdf - Page 28, https://www.mayoclinic.org/documents/mayo-pension-plan-2023.pdf - Page 20, https://mycentralstatespension.org/documents/annual-funding-notice-2023.pdf - Page 14, https://frs.fl.gov/documents/frs-pension-plan-2023.pdf - Page 17, https://fppta.org/documents/florida-pension-issues-2024.pdf - Page 23