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Cigna Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

Healthcare Provider Update: Healthcare Provider: Cigna Cigna is a global health services provider that offers a broad range of health insurance plans, including individual and family plans, employer-sponsored group plans, disability insurance, and dental, behavioral health, and pharmacy management services. Known for its commitment to connecting customers with care, Cigna also emphasizes wellness and preventive health options in its offerings. Healthcare Cost Increases in 2026 As the healthcare landscape evolves, consumers can expect substantial increases in health insurance premiums for 2026. Recent forecasts indicate that Cigna will raise individual market premiums by an average of 29.4% in states like Colorado. This surge is attributed to a combination of factors, including rising medical costs, anticipated losses of federal premium subsidies, and aggressive rate hikes across the industry. If enhanced tax credits expire as expected, over 22 million ACA marketplace enrollees could face out-of-pocket premium hikes exceeding 75%, compounding the financial strain on American families seeking affordable coverage. Click here to learn more

'Cigna employees can benefit from understanding that strategies like a Section 351 exchange, charitable donations, and tax loss harvesting may work together to help manage appreciated stock efficiently while aligning with broader long-term financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'Cigna employees should recognize that thoughtful planning with tools such as Section 351 exchanges, gifting strategies, and tax loss harvesting can help them manage highly appreciated stock while supporting both personal and philanthropic objectives.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How a Section 351 exchange can defer capital gains on highly appreciated stock.
Alternative tax-efficient strategies such as charitable donations, tax loss harvesting, and gifting.
The role of inheritance rules, step-up in basis, and combined approaches in long-term tax planning.

A Tax-Aware Q&A on How to Manage Highly Appreciated Stock

From the Section 351 exchange to other practical approaches, this Q&A addresses key considerations Cigna employees may encounter when dealing with highly appreciated shares.

Section 351 Exchange: The Fundamental Approach

Q: What is an exchange under Section 351?
A: Under certain circumstances, an investor may transfer property, such as highly appreciated shares, to a company in exchange for its stock under a provision of the Internal Revenue Code that allows the deferral of capital gains or losses.

Q: What is the primary advantage of exchanging my appreciated stock through a Section 351 exchange?
A: The main advantage is tax deferral. Gains transferred to corporations may be postponed under Section 351, though this applies only if specific diversification requirements are met, especially when transferring to investment companies like exchange-traded funds (ETFs). ¹

Q: What is meant by the “Control Test”?
A: The investor or group of investors who use their portfolio assets to fund the new entity must own at least 80% of the voting power and 80% of the total number of shares of all other classes of stock in the new company immediately after the exchange. ¹

Q: When seeding an ETF, how is the Control Test usually satisfied?
A: It is typically satisfied by either a single substantial investor making a significant asset contribution or multiple investors pooling assets to create a seeding pool for the ETF’s launch.

Q: What is the ultimate tax payment date for the deferred gain?
A: The deferred gain is recognized when the ETF shares acquired through the exchange are sold; distributions from taxable funds must also be reported in the meantime.

Other Tax-Efficient Techniques

Q: What is a straightforward method, aside from a Section 351 exchange, to sell highly appreciated shares without incurring large taxes?
A: Donating shares directly to a qualified charity is one option that some Cigna employees may benefit from.

Q: What tax advantages come with donating valuable stock to a charity?
A: Subject to holding period and adjusted gross income (AGI) limits, you can bypass capital gains taxes on the appreciation and may receive an income tax deduction for the stock’s full fair market value.

Q: What is a Donor-Advised Fund (DAF)?
A: A DAF allows you to donate appreciated stock, receive an immediate tax deduction, and then recommend grants to charities over time, while the assets in the DAF grow without tax impact. ²

Q: Can I give a family member my appreciated stock as a gift?
A: Yes. In most cases, the cost basis from the donor carries over to the recipient.

Q: Why would I give a family member in a lower tax bracket appreciated stock?
A: If they sell the stock, the lower income could result in a reduced capital gains rate, potentially as low as 0% for long-term gains. ³

Tax Loss Harvesting and Other Approaches

Q: What is harvesting tax losses?
A: Selling investments at a loss to offset gains from other sales is known as tax loss harvesting, a strategy sometimes considered by Cigna employees seeking opportunities to leverage bouts of market volatility.

Q: Can I deduct a certain amount of loss from my regular income?
A: Yes. If your capital losses exceed your gains, you can use up to $3,000 per year ($1,500 if married filing separately) to offset ordinary income, with remaining losses carried forward indefinitely. ⁴

Q: What is a Qualified Opportunity Fund (QOF)?
A: A QOF provides investors with tax incentives for investing in tracts of land designated as 'opportunity zones'. Capital gains reinvested in a QOF within 180 days of being realized can be temporarily tax deferred, while QOF investments helpd for at least 10 years may confer a permanent capital gains exclusion. ⁵ That said, 2025 legislation changes may prompt IRS updates to this rule.

Inheritance and Step-Up in Basis

Q: What is meant by a “step-up in basis”?
A: This adjusts an inherited asset’s cost basis to its fair market value at the time of the owner’s death, eliminating capital gains accumulated during their lifetime. ⁶

Q: If I gift shares while living, will I receive a step-up in basis?
A: No. The original cost basis transfers to the recipient without adjustment.

Determining the Right Strategy

Q: What is the best course of action for me?
A: The most suitable approach will depend on factors such as your gain size, income level, charitable intentions, and liquidity needs.

Q: Do any of these strategies call for professional guidance?
A: Yes. Given the complexity of the tax code, working with a qualified financial advisor and tax professional is strongly recommended before implementing these strategies.

Q: Is it possible to combine these strategies?
A: Yes. For example, you might execute a Section 351 exchange on part of your portfolio for tax-deferred rebalancing while donating another portion to a DAF for an immediate deduction.

Q: Is there a loophole in the Section 351 exchange?
A: No. This is a legitimate tax code provision designed for corporate restructuring and adapted for use in the ETF market. It is intended for tax deferral, not permanent tax elimination.

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Articles you may find interesting:

Sources:

1. Kitces. ' Using Section 351 Exchanges to Tax-Efficiently Reallocate Portfolios With Embedded Gains ,' by Ben Henry-Moreland and Brent Sullivan. 12 Mar. 2025.

2. Kiplinger. “ A Donor-Advised Fund Can Give Your Charitable Giving a Boost ,” by Samuel Gaeta. 9 May 2024.

3. Internal Revenue Service. “ Topic No. 409, Capital Gains and Losses .” IRS.gov , 8 July 2025.

4. Wealth Enhancement. ' 6 Essential Tax-Loss Harvesting Tips ,' by Jim Wiley. 6 April 2022.

5. Congressional Research Service. ' Tax Incentives for Opportunity Zones ,' by Donald Marples. 26 Apr. 2022.

6. Investopedia. “ Carryover Basis: What It Is, How It Works, Gift Taxes ,” by Julia Kagan. 16 Jan. 2023.

As an employee of CIGNA Corporation, what steps should you consider taking to understand the implications of the pension plan amendments established under recent legal interpretations? CIGNA Corporation has experienced significant changes in its pension plan, which resulted from the Amara case. In light of these changes, what should employees examine regarding their accrued benefits, and how might the historical context of these amendments impact their retirement planning?

Employees of CIGNA Corporation should thoroughly review their accrued benefits under the pension plan amendments following the Amara case, which reformed the employer's cash balance plan. It's essential to analyze how these changes affect the value of their pension benefits, especially for employees who joined the company before 1997. Understanding these amendments can significantly impact retirement planning(CIGNA Corporation_May 2…).

In what ways does the concept of ""wear-away"" as discussed in the context of CIGNA Corporation's pension plan amendments affect current employees nearing retirement? Understanding how this mechanism operates within the pension plan can help employees better strategize their retirement. Employees at CIGNA Corporation should analyze whether they could potentially experience delays in benefit accrual as a result of these changes and the legal principles that underpin them.

The "wear-away" concept, introduced in CIGNA’s pension plan amendments, can delay benefit accrual for employees nearing retirement. This mechanism often results in a period where no additional benefits are accrued, which could affect employees' retirement timing. Employees should carefully evaluate whether this delay might affect their pension expectations and strategize accordingly(CIGNA Corporation_May 2…).

How can CIGNA Corporation employees determine whether the current pension plan accurately reflects their rights under ERISA? With ongoing legal interpretations and potential reforms stemming from court rulings, employees need to assess how these rulings apply to the pension plan's amendments. This may require looking into the details of the summary plan descriptions and how to clarify their rights to future benefits.

To ensure that CIGNA’s pension plan reflects their rights under ERISA, employees should examine the summary plan descriptions and other relevant documents. Legal rulings like the Amara case can lead to reforms, so employees must clarify how these decisions impact their future benefits(CIGNA Corporation_May 2…).

What resources are available to CIGNA Corporation employees wishing to seek personalized advice regarding their specific retirement scenarios, particularly in light of changes brought about by the Amara case? Understanding the complexities of retirement benefits is crucial, and employees may benefit from tapping into CIGNAâ€™s human resource department or designated benefits counselors for guidance tailored to their circumstances.

Employees seeking personalized advice regarding retirement planning, especially in light of the Amara case, should consult CIGNA’s human resource department or designated benefits counselors. These professionals can provide guidance tailored to individual retirement scenarios, ensuring a clear understanding of pension and 401(k) options(CIGNA Corporation_May 2…).

How does the restructuring of the CIGNA Corporation's pension and 401(k) plans impact the overall retirement benefits landscape for employees who joined before and after the 1997 changes? Employees should look at the comparative advantages and disadvantages provided by both plans to make informed decisions regarding their retirement savings strategies and expected outcomes.

CIGNA employees who joined before and after 1997 should analyze the restructuring of the pension and 401(k) plans. The changes led to different retirement benefits, with cash balance plans affecting post-1997 employees. Comparing both plans’ advantages and disadvantages is crucial for making informed decisions about savings and retirement strategies(CIGNA Corporation_May 2…).

To what extent are CIGNA Corporation employees safeguarded against the financial impacts of fluctuations in interest rates in relation to their pension benefits? Employees should be aware of how the pension plan uses interest rate assumptions and their potential implications for the valuation of their pension benefits, particularly those who have been affected by the changes introduced in 1998.

Employees should understand how interest rate fluctuations impact the valuation of their pension benefits, especially those affected by the 1998 changes. Interest rate assumptions play a crucial role in determining the value of cash balance pensions, and employees must stay informed about these variables(CIGNA Corporation_May 2…).

What procedural steps must CIGNA Corporation employees follow to contest any discrepancies or misunderstandings about their pension benefits? Knowledge of CIGNA Corporation's dispute resolution process can empower employees to take action when they feel their rights have not been adequately represented or upheld, particularly in the wake of significant plan amendments.

To contest discrepancies in their pension benefits, CIGNA employees must follow the dispute resolution procedures laid out by the company. This process is especially important after the significant amendments resulting from the Amara case, as employees may need to defend their rights to accrued benefits(CIGNA Corporation_May 2…).

How has the legal environment surrounding pension plans, particularly through cases like the Amara lawsuit against CIGNA Corporation, influenced the benefits structure offered to employees? This question encourages employees to explore how changes at the judicial level redefine what retirement benefits can look like and the implications for their long-term financial security.

The Amara lawsuit influenced CIGNA’s pension structure by leading to a judicial reformation of the pension plan. Employees should explore how these legal decisions have reshaped the benefits landscape, as it directly affects their long-term financial planning and retirement security(CIGNA Corporation_May 2…).

What specific changes in eligibility criteria for early retirement benefits should current CIGNA Corporation employees be aware of, especially regarding the transition to the cash balance plan? Employees need to scrutinize the implications of these changes and how they may affect their decisions about early retirement and associated benefits.

Employees should be aware of changes to early retirement eligibility resulting from the transition to a cash balance plan. These adjustments, introduced after 1997, may alter the terms under which early retirement benefits are accessible, impacting decisions about retirement timing(CIGNA Corporation_May 2…).

How can CIGNA Corporation employees effectively reach out to the HR department or benefits specialists to get more information about their retirement options? Understanding the channels of communication established within the company for discussing benefits will be crucial for employees seeking clarity on their rights and the provisions of the pension plan following the recent amendments.

CIGNA employees can reach out to the HR department or benefits specialists for more information on their retirement options. These channels provide crucial insights into pension plan amendments and can clarify how the Amara case and other legal changes affect employees’ retirement benefits(CIGNA Corporation_May 2…).

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

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Cigna offers RSUs and stock options to certain employees. The RSUs vest over a specific period, encouraging retention.