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5 Tax Moves Sears Holdings Employees Should Make Before Year-End

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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 can maximize year-end planning by using credit card usage for deductible expenses and charitable donations that provide immediate tax benefits and long-term financial security, 'said Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement Group.

Adjusting withholdings, using IRA strategies and Qualified Charitable Distributions can help Sears Holdings employees avoid penalties and achieve a comfortable retirement, said Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement Group.

In this article we will discuss:

1. Strategies to optimize Sears Holdings financial planning before the year ends.

2. Tax-saving ideas: strategic credit card use & charitable donations.

3. Techniques for long-term financial security - IRA borrowing and Social Security planning.

When it comes to Sears Holdings financial planning, implement strategies to optimize your fiscal health as the year winds down. This article details novel strategies to consider before December 31st to improve financial position with Sears Holdings.

Use of Strategic Sears Holdings Credit Cards.

Contrary to the conventional advice to cut back on credit card use, a prudent strategy involves using them to pay for deductible expenses. The tax benefit occurs on the date of charge, not on payment. That's especially useful for tax-deductible expenditures like real estate taxes and philanthropic contributions, provided they remain below USD 10,000. By following a monthly balance payment schedule, this approach maximizes tax deductions and takes advantage of credit card points without paying interest.

Charitable Contributions Through Decluttering

Often overlooked is getting Sears Holdings tax deductions for donating old personal items. And it's a tax benefit too. It involves recording the donated items, getting a receipt and ensuring the total worth is not more than USD 5,000, to avoid an appraisal. The deduction is equal to the current value of the item or its original price, whichever is less.

Adjusting Withholdings

Sears Holdings employees with supplemental income sources like side work must adjust their tax withholdings to avoid penalties. In increasing penalties for underpayment to 8%, the Internal Revenue Service stresses the need to pay at least 90% of an annual tax obligation by year's end. Withholdings are considered to have been uniformly applied throughout the year so one could potentially avoid such penalties by strategically enhancing withholdings near the end of the year.

Property Tax Payment Strategy

A USD 10,000 cap on state and local tax deductions and current interest rates over 5% on savings accounts have reduced the financial appeal of prepaying property taxes. Keep consistent payment schedules to maximize interest earned on savings accounts.

Use IRA for Short Term Liquidity.

When pressed for cash, borrowing from an IRA may be the smart move. That means repaying the borrowed funds within sixty days and only once every twelve months. Conforming to these regulations carries no penalty or tax.

Integrating Traditional End-of-Year Financial Moves.

These suggestions offer new perspectives, but should be used in addition to conventional end-of-year financial procedures rather than in place of them. The above strategies include grouping itemized deductions, optimizing contributions to Sears Holdings retirement accounts, maximizing medical savings accounts, evaluating Roth conversions, establishing donor-advised funds and capital loss harvesting.

Remember these recommendations should be considered supplements to your full Sears Holdings financial plan. You should consult a Certified Public Accountant (CPA) to tailor these recommendations for your specific financial situation. With the end of the year approaching, proactive financial planning measures may provide significant long-and short-term benefits.

Persons approaching or retiring from Sears Holdings - especially those around age 60 - need to understand Social Security benefits in terms of tax planning. Knowing when to start getting Social Security benefits is critical. Beneficiaries with large retirement accounts or other sources of income could see a big boost in their monthly benefit by delaying SS start age 70. This can maximize tax efficiency and long term financial stability. Postponing benefits until full retirement age of 70 produces an estimated 8% increase in benefits annually, according to a report from the Social Security Administration in 2021.

Year-end tax planning is like preparing a garden for winter. In the same way an arboriculturist trims excess vegetation, prunes undesirable plants and urban gardens late-season harvest crops, retirees should also carefully prune taxable income, trim unnecessary expenditures and sow the seeds of future financial development. By applying the credit cards toward deductible expenses, one prunes the tree for better growth the following year. Donating unused items is like pulling vegetation; It takes away unnecessary things and adds to the charitable soil. Strategic cash flow management through IRA adjustments, deferring property tax prepayments and manipulating withholdings is like sowing winter crops; They require some anticipation of seasonal changes, but provide for a good harvest of savings and financial security in retirement.

Added Fact:

In addition to the strategies above, Sears Holdings employees can take advantage of a qualified Charitable distribution (QCD) option in their IRA - For those age 70 1/2 or older - that allows direct transfers of up to USD 100,000 per year to a qualified charity without the Distribution being taxable income. That move meets the year's Required Minimum Distribution (RMD) and may lower the retiree's income tax bracket, but also supports charitable causes without affecting the taxpayer's adjusted gross income. This strategy, which can be useful to retirees looking for tax-efficient ways to give to charity, was highlighted in IRS guidelines for 2021, highlighting its value in retirement and tax planning.

Added Analogy:

An experienced captain navigating year-end tax planning for Sears Holdings employees is like navigating the maze of retirement. So just as a captain uses charts, compasses and the stars to navigate, employees must use strategic tax moves to steer their financial ship toward retirement success. Use credit card strategies for deductible expenses like sailing with a good wind that blows the ship forward. Donating unused items suggests shedding unnecessary pounds for speed and agility.

It's like tuning the course of a vessel by changing withholdings and managing property taxes. Borrowing from an IRA for liquidity is like having a reserve tank of fuel for those moments of need. As a captain might use such tools alongside more conventional navigation methods, so too can using such tax strategies alongside more traditional financial planning deliver a smooth ride toward financial security and a comfortable retirement. With each move comes a little adjustment to the sails so retirees and those approaching retirement can move into the next chapter confidently and safely.

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Sources:

1. J.P. Morgan Private Bank. '5 Tax Planning Actions to Take Before Year-End.'  J.P. Morgan Private Bank , October 2024, pp. 1-3.

2. SmartAsset. 'Retirement Tax Strategies to Consider.'  SmartAsset , December 2024, pp. 2-4.

3. Ed Slott and Company, LLC. 'Using Your IRA for a Short-Term Loan.'  Ed Slott and Company , May 2024, pp. 1-2.

4. Fortune. 'Tax Tips for HENRYs: 5 End-of-Year Moves if You Are High Earner Not Yet Rich.'  Fortune , November 2024, pp. 1-2.

5. Yahoo Finance. '4 Ways to Save on Taxes in Retirement.'  Yahoo Finance , February 2025, pp. 1-3.

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

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