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HF Sinclair Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

Healthcare Provider Update: Offers medical plans through Blue Cross Blue Shield of Texas (BCBSTX), with options for PPO and HDHP plans, plus dental (BCBSTX), vision (VSP), and virtual care via MDLIVE 1. As ACA premiums rise and subsidies expire, HF Sinclairs employer-sponsored plans with preventive care and wellness incentives may help employees avoid the steep out-of-pocket costs expected in the marketplace. Click here to learn more

'HF Sinclair 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.

'HF Sinclair 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 HF Sinclair 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 HF Sinclair 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 HF Sinclair 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.

Featured Video

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.

What is the 401(k) plan offered by HF Sinclair?

The 401(k) plan at HF Sinclair is a retirement savings plan that allows employees to save a portion of their paycheck before taxes are deducted.

How can I enroll in HF Sinclair's 401(k) plan?

Employees can enroll in HF Sinclair's 401(k) plan by completing the enrollment process through the company's benefits portal or by contacting the HR department for assistance.

Does HF Sinclair match employee contributions to the 401(k) plan?

Yes, HF Sinclair offers a matching contribution to the 401(k) plan, which helps employees boost their retirement savings.

What is the maximum contribution limit for HF Sinclair's 401(k) plan?

The maximum contribution limit for HF Sinclair's 401(k) plan is set according to IRS guidelines, which may change annually. Employees should check the latest limits for the current year.

When can I start contributing to HF Sinclair's 401(k) plan?

Employees at HF Sinclair can start contributing to the 401(k) plan after completing their eligibility period, which is typically outlined in the benefits documentation.

What investment options are available in HF Sinclair's 401(k) plan?

HF Sinclair's 401(k) plan offers a variety of investment options, including mutual funds, stocks, and bonds, allowing employees to choose based on their risk tolerance and retirement goals.

Can I take a loan against my 401(k) at HF Sinclair?

Yes, HF Sinclair allows employees to take loans against their 401(k) savings, subject to certain conditions and limits as outlined in the plan documents.

What happens to my 401(k) if I leave HF Sinclair?

If an employee leaves HF Sinclair, they have several options for their 401(k), including rolling it over to a new employer's plan, transferring it to an IRA, or cashing it out (with potential penalties).

How often can I change my contribution amount to HF Sinclair's 401(k) plan?

Employees can typically change their contribution amount to HF Sinclair's 401(k) plan during open enrollment periods or at any time as permitted by the plan rules.

Is there a vesting schedule for HF Sinclair's 401(k) matching contributions?

Yes, HF Sinclair has a vesting schedule for its matching contributions, meaning employees must work for a certain period before they fully own the matched funds.

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

HF Sinclair provides both a pension plan and a 401(k) plan for its employees. The company's pension plan is referred to as the HF Sinclair Retirement Plan, and it generally requires employees to meet certain age and years of service qualifications to be eligible. The pension formula is based on a final average pay calculation, which considers the employee's average salary over the last few years of service. For the 401(k) plan, known as the HF Sinclair 401(k) Retirement Savings Plan, employees are automatically enrolled with a default contribution rate of 6% of eligible earnings. Employees have the flexibility to adjust this contribution rate from 1% to 75% of their eligible earnings. The plan includes a company match, enhancing the retirement savings for participants. Detailed information about the pension and 401(k) plans, including eligibility criteria, contribution limits, and specific terms, can be found in the HF Sinclair benefits summary documents from 2022 to 2024, accessible through their internal benefits portal. Please refer to the specific benefits document for exact details, including page numbers

Layoffs: In 2023, HF Sinclair implemented significant layoffs at its Sinclair refinery, affecting nearly 100 employees. The decision was met with concern from both state and federal officials due to the economic impact on local communities. This reduction aligns with the company's broader strategy to optimize operations in a challenging economic environment. The layoffs are important to address given the current economic pressures and the impact on the local workforce, emphasizing the need for strategic planning and support for affected employees.

HF Sinclair Corporation offers various employee stock options (ESOs) and Restricted Stock Units (RSUs) as part of its equity compensation program. These options and units are made available to employees to align their interests with the company's performance and long-term success. Stock Options: HF Sinclair provides employees the opportunity to purchase company stock at a predetermined price, known as the exercise price. This option typically vests over a period of time, allowing employees to purchase shares at the set price, regardless of the market price at the time of exercise. Restricted Stock Units (RSUs): RSUs are another form of equity compensation offered by HF Sinclair. Unlike stock options, RSUs represent a promise to deliver company shares at a future date, subject to vesting conditions such as continued employment or performance milestones. Upon vesting, RSUs are converted to actual shares of HF Sinclair stock. Eligibility: Both stock options and RSUs are generally made available to a wide range of employees within HF Sinclair, including senior executives, managers, and other key employees. The availability of these equity awards is typically tied to the employee's role, performance, and tenure with the company. In 2022, 2023, and 2024, HF Sinclair continued to issue these equity compensations as part of their incentive plans, adapting the terms and conditions based on the company’s financial performance and strategic goals. For detailed information on the specific terms and conditions, including vesting schedules and eligibility, you can refer to the company’s investor relations presentations and annual reports.

HF Sinclair offers a comprehensive range of health benefits aimed at supporting the physical, mental, and financial well-being of its employees. For the years 2022, 2023, and 2024, HF Sinclair's health benefits include medical plans with Health Savings Accounts (HSA), Health Reimbursement Accounts (HRA), and incentives like the "Go-to-Doctor" program, which offers premium discounts for completing an annual physical. Employees have access to various healthcare plans, including dental and vision coverage, as well as wellness programs that promote preventive care.

Additional Articles

Check Out Articles for HF Sinclair employees

For more information you can reach the plan administrator for HF Sinclair at , ; or by calling them at .

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