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

Sears Holdings Families: Why a Letter of Instruction Can Simplify Estate Planning

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 bring more clarity to their estate plans by using a well-organized letter of instruction, which is a practical way to help families navigate important decisions with greater confidence.' — Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

'Sears Holdings employees can create a smoother transition for their families by using a clear letter of instruction, which can be an effective way to support loved ones during estate administration.' — Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

Why a letter of instruction can support your estate plan.
What to include in a letter of instruction.
How Sears Holdings employees can use a letter of instruction to help streamline estate administration.

Important Lessons

Estate planning documents like a will and a revocable trust are important, but they might not give your family all the information they need to handle your affairs when you pass away, especially for Sears Holdings employees with complex benefits.

In addition to an estate plan, a letter of instruction can offer your loved ones more information about your assets and personal preferences.

A letter of instruction can contain additional details, such as burial plans and the placement of essential documents, but it should not conflict with your estate planning documents.

Your loved ones might not know who to call, where to find your assets, or how to recognize reputable creditors if something were to happen to you today. By providing clear, supplemental guidance, a letter of instruction can help reduce the stress and work involved in the estate administration process.

A Letter of Instruction: What Is It?

A letter of instruction is an informal document outlining your assets and last wishes, sent to an executor, personal representative, or family members. It adds helpful information not included in legally binding estate planning documents like a will or revocable trust. For Sears Holdings employees managing multiple retirement and savings plans, a letter of instruction can help simplify administration for family members, even though it is not legally required.

Since this letter is informal, it can be updated without consulting an attorney as circumstances change over time. It can contain supplementary information that supports your estate plan, but it should not contradict anything in your legal estate planning documentation.

How to Compose an Instructional Letter

Funeral Plans

You might provide information about your preferred funeral or burial type, funeral home, clergy member, music, speakers, or tribute. You can also include details about pre-paid or pre-arranged funeral or burial plans and where related paperwork is located. Some people also provide biographical details—something Sears Holdings retirees can include for clarity.

Crucial Records

You can note the location of your Social Security card, recent bank account statements, deeds, titles, mortgage documents, important records, and estate planning documents. Some individuals also indicate where to find recent tax returns, which may help identify assets or income sources. If these documents are stored in a lockbox or vault, providing access instructions may be helpful.

Contact Details for Financial Representatives

The names and contact information for bankers, tax preparers, lawyers, insurance agents, real estate agents, and financial advisors can be included in the letter. These professionals can assist with background information, asset identification, account transfers, and final tax filings.

Details of the Assets

You can list your assets’ locations, titling, identifying details, and current values. This may include real estate, stock certificates, savings bonds, annuities, time shares, bank accounts, brokerage accounts, retirement accounts, company interests, safe deposit boxes, life insurance, and personal belongings with monetary or sentimental value.

Computer Files and Online Accounts

You may wish to list your digital files and accounts and designate a successor in your estate planning documents to manage them, since state and federal laws may limit access without written approval. For Sears Holdings retirees who store retirement and benefits information online, this documentation may help reduce challenges.

Details of Debt

You can include information regarding your debts, such as account numbers, balances, statements, and lender contact details.

Beneficiary Details

The beneficiaries listed in your estate plan, along with their contact details, may be included in the letter. This makes it easier for an executor to locate and communicate with those who will receive assets—an important step for families with Sears Holdings retirement accounts.

Pets

You can specify who you want to care for your pets and any specific instructions if your estate documents do not mention them. You may also include your veterinarian’s contact information.

Distribution List for Personal Property

Some states allow individuals to draft a separate document listing specific items of tangible personal property and their intended recipients, as long as the will references the list. Even in states where this is not legally binding, a letter of instruction can still guide your executor and help minimize disagreements.

Private Notes and Clarification of Goals

Some people include private notes or explanations for their decisions regarding inheritance or financial principles. Although not legally binding, these notes can help prevent misunderstandings.

What Does a Letter of Instruction Not Need to Include?

A letter of instruction should not repeat information already found in your estate planning documents. It is intended to provide additional details only.

It also should not be used to make changes to legally enforceable estate documents. Informal updates are not binding and may create conflicts.

Where to Store Your Instruction Letter

You can keep a copy of the letter with your estate planning papers, provide one to your lawyer, or place it somewhere your family is likely to look first. You can also share a copy with your executor and discuss it with them if you feel comfortable. Updating the letter each year is useful as assets and personal information change—particularly for Sears Holdings employees with evolving retirement benefits.

Do You Need Guidance?

The Retirement Group can help you prepare for retirement if you are updating or creating your estate plan and want assistance organizing your family’s financial information. Call us at (800) 900-5867 .

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Articles you may find interesting:

Sources:

1. Parker, Craig. “How to Write a Letter of Instruction: A Step-by-Step Guide.” Trust & Will, n.d.,
https://trustandwill.com/learn/how-to-write-a-letter-of-instruction . Accessed 1 Dec. 2025.

2. AARP Education & Outreach. “State Your Intentions With a Letter of Instruction.” AARP, 9 Nov. 2022,
https://www.aarp.org/money/retirement/letter-of-instruction/ . Accessed 1 Dec. 2025.

3. Kuffel, Hunter. “Writing a Letter of Instruction for Your Estate Plan.” SmartAsset, 12 Oct. 2025,
https://smartasset.com/estate-planning/letter-of-instruction . Accessed 1 Dec. 2025.

4. McDonald Jacobs. “Letter of Instruction in Estate Planning.” McDonald Jacobs: Portland, Oregon Accountants & Business Consultants, n.d.,
https://www.mcdonaldjacobs.cpa/letter-of-instruction-in-estate-planning/ . Accessed 1 Dec. 2025.

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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