Walt Lupeika - Newsletters

The IRS has issued final regulations modifying reporting obligations for partnerships involved in Code Sec. 751(a) exchanges of partnership interests. The regulations remove the requirement that partnerships furnish transferors with certain information relating to unrealized receivables and inventory items by January 31 following the exchange year. The regulations are effective for returns filed for tax years ending on or after May 20, 2026.

Under Code Sec. 6050K, partnerships must file Form 8308, Report of a Sale or Exchange of Certain Partnership Interests, for transfers involving Code Sec. 751(a) property. The IRS and Treasury Department received comments that many partnerships could not determine the information required for Part IV of Form 8308 by the January 31 furnishing deadline. As a result, the final regulations remove Reg. §1.6050K-1(c)(2) and revise Reg. §1.6050K-1(c)(1) to permit partnerships to furnish Form 8308 completed in accordance with the form instructions.

Although partnerships are no longer required to furnish Part IV information to transferors and transferees by January 31, they must still file a completed Form 8308, including Part IV, with Form 1065. The IRS finalized the regulations without substantive changes from the proposed regulations issued in 2025.

T.D. 10048

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The IRS has issued guidance on qualified long-term care distributions from qualified retirement plans. The guidance affects providers of certified long-term care insurance (issuers), plan administrators, and individual participants receiving qualified long-term care distributions. The IRS also extended the general deadline for amending a plan to permit qualified long-term care distributions to December 31, 2027.

Background

The SECURE 2.0 Act of 2022 (SECURE 2.0 Act), permitted defined contribution plans to make qualified long-term care distributions, effective for distributions made after December 29, 2025. The 10 percent additional tax on early distributions would not apply to distributions under Code Sec. 401(a)(39). However, a qualified long-term care distribution would be included in the taxpayer’s gross income.

Disclosure Requirements

The guidance addresses content requirements and procedures for submitting an Issuer Disclosure to the IRS. There is no general deadline for submitting an Issuer Disclosure. However, an issuer must submit an Issuer Disclosure to the IRS before the issuer can file a long-term care premium statement with a defined contribution plan.

Distribution Requirements

Under the guidance, the plan administrator is permitted to rely on the issuer’s statement and the information provided on the long-term care premium statement in making a qualified long-term care distribution. It is optional for a plan to permit qualified long-term care distributions, but the exception to the 10% additional tax only applies if the plan permits qualified long-term care distributions, even if the employee uses a distribution to pay for long-term care insurance. Unlike other permitted distributions, a qualified long-term care distribution would not be eligible for an extended 3-year repayment to a retirement plan.

Reporting Requirements

The payment of a qualified long-term care distribution to an employee must be reported by the payor on Form 1099-R, Distributions from Pensions, Annuities, Retirement or Profit Sharing Plans, IRAs, Insurance Contracts, etc.

Further, issuers must make a return to the IRS using Form 1099-LPS, Long-Term Care Premiums Paid Statement. The issuer will report the long-term care premiums paid for the calendar year. The Form 1099-LPS must be filed with the IRS no later than February 1 of the calendar year following the calendar year the long-term care premium statement was filed with the plan.

Deadline Extension

The guidance extends the deadline for a plan sponsor of a defined contribution plan that is not a governmental plan, a section 403(b) plan maintained by a public school, or an applicable collectively bargained plan, to amend its plan to permit qualified long-term care distributions from December 31, 2026, to December 31, 2027. The deadlines to amend defined contribution plans that are applicable collectively bargained plans or governmental plans remain as provided in Notice 2024-02. Thus, Notice 2024-2, I.R.B. 2024-2, 316, is modified in part.

Notice 2026-33

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The IRS finalized regulations treating income derived by individual members of an Indian tribe from fishing rights-related activities as compensation for purposes of limitations on benefits and contributions under a qualified retirement plan. These regulations are effective for plan years beginning on or after May 4, 2026, and affect participants, beneficiaries, sponsors, and administrators of Tribal plans.

Fishing rights-related income is exempt from federal income tax and employment tax under Code Sec. 7873. However, proposed reliance regulations would allow contributions to be made to qualified retirement plans based on fishing rights-related income. Also, plans that accept contributions of fishing rights-related income may still use safe harbor definitions of compensation. The IRS finalized this rule as proposed without material modification.

Although the final rule is somewhat limited in scope, the IRS addressed additional issues in the preamble. The IRS clarified that plan contributions attributable to a Tribal employee's fishing rights-related activiity is treated as investment in the contract under Code Sec. 72 . Thus, distributions of the amount contributed would generally be tax-free (subject to basis recovery rules) and distributions attributable to earnings would be taxable. The IRS also indicated that plans that permit designated Roth contributions may allow contributions attributable to fishing rights-related activity to be made on a Roth basis.

T.D. 10046

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The IRS has introduced a streamlined option allowing taxpayers to extend the time to challenge disallowed Employee Retention Credit (ERC) claims, reducing the need for immediate refund litigation. The measure applies to taxpayers who received Letter 105-C or 106-C, are awaiting review by the IRS Independent Office of Appeals and have six months or less remaining in the statutory two-year period.

Taxpayers generally have two years from the disallowance notice to resolve the claim or file a refund suit, but an administrative appeal does not suspend this deadline. Once the period expires, the IRS cannot issue a refund even if the taxpayer later prevails. To address this, eligible taxpayers may execute Form 907, Agreement to Extend the Time to Bring Suit, provided it is signed by both parties before the limitation period ends.

The IRS now permits submission of Form 907 through its Document Upload Tool, with qualifying requests reviewed and confirmed in writing. While the IRS is issuing notices to eligible taxpayers, others meeting the criteria may also apply. The agency indicated that the initiative is intended to preserve taxpayer rights and facilitate administrative resolution of ERC disputes.

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The IRS has established a significant issue ruling program for cerain corporate transactions (Rev. Proc. 2026-21). This program would not diminish the availability of letter rulings under existing programs. This procedure modifies and amplifies the ruling procedures provided in Rev. Proc. 2026-1, I.R.B. 2026-1, 1, and Rev. Proc. 2026-3, I.R.B. 2026-1, 143.

The significant issue ruling program allows taxpayers to request rulings on one or more issues that:

are solely under the jurisdiction of the Associate Chief Counsel (Corporate);
are significant issues, as defined in section 4.02 of Rev. Proc. 2026-21; and
involve the tax consequences or characterization of a transaction (or part of a transaction) that is described in Code Sec. 332, 351, 355, 368, or 1036.

Significant Issue Ruling Program

Taxpayers may request, and the IRS may issue, a ruling on part of an integrated transaction described in the above provisions, or a ruling on a particular legal issue under a section of the Code or regulations with respect to a transaction (or part thereof) rather than a ruling that addresses all aspects of that section (or any other section) with respect to the transaction (or part thereof).

In addition, the IRS may rule on the tax consequences resulting from integrated transactions described in the above provisions to the extent that a significant issue is presented under related Code sections that address such tax consequences.

A significant issue generally is a germane and specific issue of law, provided that a ruling on the issue would not be a comfort ruling or the conclusion in such a ruling otherwise would not be essentially free from doubt.

The requests for ruling must contain (1) narrative description of the transaction that puts the significant issue in context; (2) statement identifying the issue; (3) analysis of the solvability of issue; and more.

Effect on Other Documents

Rev. Proc. 2026-1 and Rev. Proc. 2026-3 are modified and amplified.

Effective Date

The significant issue ruling program applies to all letter ruling requests described in section 4.01 of Rev. Proc. 2026-21 postmarked or, if not mailed, received by the IRS after May 5, 2026.

Rev. Proc. 2026-21

Other References:

Code Sec. 332
CCH Reference - FED ¶16,052.188

Other References:

Code Sec. 351
CCH Reference - FED ¶16,405.48

Other References:

Code Sec. 355
CCH Reference - FED ¶16,466.923

Other References:

Code Sec. 368
CCH Reference - FED ¶16,753.53

Other References:

Code Sec. 1036
CCH Reference - FED ¶29,702.11

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The IRS has announced a new time-limited settlement opportunity for eligible taxpayers involved in conservation easement and historic preservation easement disputes with the IRS. The program aims to resolve cases faster and on terms that are generally more favorable than recent Tax Court decisions.

The IRS has announced a new time-limited settlement opportunity for eligible taxpayers involved in conservation easement and historic preservation easement disputes with the IRS. The program aims to resolve cases faster and on terms that are generally more favorable than recent Tax Court decisions. Since 2020, the IRS has settled 405 cases through earlier initiatives, although taxpayers still had to pay penalties and were allowed only limited deductions for certain out-of-pocket costs. More than 1,100 conservation easement cases currently remain pending before the IRS and the Tax Court. Under the new initiative, many eligible partnerships will not have to make an upfront payment to participate. In addition, taxpayers whose earlier settlement offers expired or were rejected may now have another chance to resolve their cases, while some partnerships that were not previously eligible may also qualify. IRS Chief Executive Officer Frank J. Bisignano said Congress created the conservation easement deduction to encourage legitimate preservation efforts rather than tax shelters based on inflated property values.

The IRS said partnerships that accept the offer during the initial 90-day period generally will not be allowed a charitable contribution deduction, but they may qualify for a limited deduction tied to certain out-of-pocket expenses. Those partnerships generally would face a 10 percent gross valuation misstatement penalty, while partnerships settling during an additional 45-day period generally would face a 20 percent penalty. Interest also will continue to accrue as required by law. At the same time, the IRS noted that courts have repeatedly reduced claimed deductions and upheld significant penalties in conservation easement disputes. Certain cases, such as those already tried or currently under appeal, will not qualify for the initiative. The IRS added that eligibility will depend on the status and specific facts of each case.

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Following a 2026 tax filing season that was consistent with the 2025 season, the American Institute of CPAs offered legislators a series of recommendations to help improve filing season in the future.

“Based on limited and anecdotal information, many practitioners noted that the IRS appeared to operating consistently compared with the prior year’s service,” AICPA said in a recent letter to the Senate Finance Committee’s top leadership following a hearing on the 2026 tax filing season, adding that data currently available shows “tax return processing remained relatively consistent, though the quality of telephone services appeared to vary depending on the hotline.”

AICPA did observe that while Internal Revenue Service modernization efforts have allowed for consistent customer service levels compared to recent prior years, “IRS customer service has not returned to pre-COVID-19 pandemic levels according to IRS data and the AICPA’s most recent annual membership survey.”

With that, the industry organization offered recommendations in the areas of governance and oversight, taxpayer services, and dedicated practitioner services.

In the area of IRS governance and oversight, AICPA recommended the following:

Requiring a Government Accountability Office review to determine whether a private sector board with sufficient authority to hold the IRS accountable and oversee implementation of key recommendations from advisory groups;
Re-establish the annual joint hearing review to focus on strategic and business plans, taxpayer service and compliance, technology and modernization, and the filing season; and
The Joint Committee on Taxation should provide a bi-annual report on the overall state of the Federal tax system.

In the area of taxpayer service, the following recommendations were offered:

Hire more qualified and experienced professionals from the private sector, adequately train all agency employees, skillfully manage IRS resources, and ensure organizational alignment between Congress, the executive branch, and the IRS;
Congress should determine what the appropriate level of service is and then ensure that the appropriate resources are allocated to achieve that level;
Continue to improve the technology infrastructure modernization; and
Effectively utilize customer satisfaction surveys to assess IRS performance, improve the taxpayer experience, and effectuate modernization efforts or process improvement.

AICPA pushed for the passage of the Taxpayer Assistance and Services Act, which it states “would significantly improve IRS services, reinforce fairness and transparency in our tax system, and reduce tax administrative burdens on taxpayers and practitioners, including many critical tax provisions for which AICPA has previously advocated.”

In the area of dedicated practitioner services, AICPA recommended:

Create consolidated dedicated “executive-level” practitioner services comparable to private sector services that are implemented and adapted based on practitioner feedback solicited periodically; and
Continue to expand the functionality of a robust and enhanced tax professional account as part of the IRS’s online portal with account access to all of a practitioner’s client information, allowing for IRS to communicate directly with authorized practitioners, enable a centralized login system, and prioritize the protection and privacy of user identities and data;
Provide practitioners with a robust practitioner priority hotline with high-skilled employees capable of resolving complex technical and procedural issues; and
Assign customer service representatives to each geographic area to address unusual or complex issues that practitioners were unable to resolve through the priority hotlines.

The letter to the Senate Finance Committee leadership and other AICPA 2026 tax policy and advocacy comment letter can be found here.

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Telecommuting not only offers employees flexibility, but accommodates lives that can often be hectic. While employees love the lifestyle and family/home advantages of telecommuting, the potential improvement to the bottom line is what appeals to employers.

Telecommuting not only offers employees flexibility, but accommodates lives that can often be hectic. While employees love the lifestyle and family/home advantages of telecommuting, the potential improvement to the bottom line is what appeals to employers. For example, turnover may decrease as satisfied employees are less likely to jump ship; absences may decrease since inclement weather and sick children do not prevent a home-bound employee from working; and overhead is reduced as less office space and support staff are required. Employees also enjoy financial benefits as they find their expenses for clothing, lunch and commuting are drastically reduced.

Tax implications of telecommuting

Although it may not be a top consideration as you and your employees contemplate the desirability of telecommuting, the question should nevertheless be addressed: what is the tax effect of such an arrangement?

Employer

If your employees telecommute, you probably won't feel a thing. The employee is paid just as he would be if he were on-site; the collection and payment of employment taxes will still be your responsibility as the employer; supplies and computer that you provide will still be deductible as an ordinary and necessary business expense.

Employee

But what about a telecommuting employee? Can telecommuting lead to an increase or decrease in net income? A change in deductions? An increase in the amount and types of required recordkeeping? The answer is yes... to all of the above.

Home office deduction. A discussion of telecommuting deductions should begin with the telecommuter's home office. A home office offers not only the possibility of a tax deduction in and of itself; it also affects the employee's ability to deduct other items that he may provide in order to do his job, such as computers and peripherals.

Strict requirements are applied by the IRS to home offices: expenses of the office are deductible only if certain conditions are met. The area used for business must be used (1) for the convenience of his employer and (2) regularly and exclusively as a principal place of business (or as a place to meet with clients or customers, but that will not usually be the case for a telecommuting employee).

Convenience of the employer. When is an employee's home office used for the "convenience of the employer"? Courts, taxpayers and the IRS have struggled with this issue. The U.S. Supreme Court has said that it is a response to a business necessity. This test is satisfied if it is the employer who wants the arrangement. It is possible, however, that if it is the employee who asks for telecommuting, the IRS will conclude that the arrangement is not for the convenience of the employer. If your employee plans to take a home office deduction, it will be easier for him to meet the test if your records document that you requested the arrangement or that you mutually decided that telecommuting was preferred.

Principal place of business. If the convenience of the employer test is met, the employee still has to show that his home office is his principal place of business. If he strictly telecommutes, this should not be a problem. If he alternates between his home office and your office location, he will meet this test if (1) he uses his home office for administrative and management activities related to the business and (2) there is no other place where he conducts substantial activities of this type. If this test doesn't produce a clear answer, the determination will have to be made based on (1) which location he spends more time at and (2) the relative importance of the business activities he conducts at both.

If the home office qualifies for deduction, all of the expenses relating to the office and its use may be deductible. These expenses include direct expenses, such as repairs to the room, installation of carpeting, etc. and indirect expenses, which relate to the office as part of the entire house, such as utilities, rent or mortgage interest, real estate taxes, etc. If the employee's income from the business use of his home equals or exceeds total business expenses, all of the expenses can be deducted.

Deducting computers and peripherals. How a telecommuting employee treats computers and related equipment depends on whether these items are the property of the employer or the employee.

Supplied by employer. If the employer supplies them, he is entitled to deduct the cost. The tax result to the employee is less clear. It is possible, and in fact most likely, that the items will simply be treated as any other untaxed supplies and equipment provided to on-site employees to do their job, like paper and pens and a desk.

Alternatively, although it is difficult to support an argument that an employee's use of a computer in doing business for his employer should be treated as a fringe benefit, this is relatively new territory for the IRS and it has not officially tackled the issue. If employee non-office business use of employer-provided equipment is determined to be covered by the Internal Revenue Code, it seems likely that it would be treated as an excludable working condition fringe benefit. If so, employees will have to substantiate their business use in order to qualify for the exclusion. And what about an employee's personal use of the employer's computer? If the employee who uses an employer-provided computer can substantiate his business use of the computer and if his personal use is minimal, that benefit may be a de minimis fringe benefit he can exclude from taxation.

Supplied by employee. If the computer is supplied by the employee, he can expense or depreciate the computer if it is both (1) required as a condition of employment and (2) used for the convenience of the employer. Qualifying for the home office deduction operates somewhat as a safe harbor for computer-related deductions. If the employee couldn't satisfy the requirements for a deductible home office, he will have to substantiate his business use in order to depreciate the computer and/or deduct related expenses. Substantiation requires the employee to keep adequate records documenting the time and amount of the business use, the date of expenditure or of use of the computer, the business purpose of the use of the computer, and the amount of each expenditure respecting the computer, such as the acquisition cost. If he met the requirements for taking a home office deduction, however, he does not have to substantiate the business use of the computer. Regardless, if the computer is not acquired or used by the employee as a condition of his employment and for the convenience of his employer, he can't depreciate or expense it. In addition to these requirements, computer expenses, just like all other business expenses, must be ordinary and necessary.

If the employee does use the computer for the employer's convenience and as a condition of his employment but can't meet the requirements for a home office deduction and must substantiate his business use in order to depreciate or deduct his computer, the amount deductible will be that proportion of expenses that correlates to the business use of the computer. The depreciation method available to the telecommuting employee will depend on whether the computer or other related equipment is used more or less than 50% for business. If more than 50%, he can use MACRS 200% declining balance depreciation for the business-use portion of the property plus that portion of the computer he personally used in the production of investment, royalty or rental income. If business use was less than 50%, the employee is limited to the straight-line method of depreciation. If the employee wants to expense the computer, he can only do so if its business use was more than 50%, and then he can expense only that portion of the property that was allocated to business use.

Dealing with reimbursed expenses. What about employer-reimbursed expenses? A telecommuting employee may be reimbursed for utilities, phone expenses or similar charges related to his home office and may be supplied with office materials or other supplies. All of these amounts will be considered either (1) employer owned items used in performing the employer's work and not income to the employee or (2) working condition fringe benefits and tax-free to your employee if he could deduct them as ordinary and necessary business expenses if he had paid them himself. In order to categorize these amounts as working condition fringes, the employee must be able to establish his home office as his principal place of business.

Telecommuting is increasing in acceptance and favor as a work option providing significant benefits to employee and employer alike. As its use expands, employers and employees should be aware that there is more to telecommuting than reduced costs and a more relaxed lifestyle. Careful and creative tax planning will help avoid any surprises or pitfalls.

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Q. I am reviewing my portfolio and considering selling some of my stock. How do I determine what tax basis I have in the publicly-traded shares that I own for purposes of determining my gain or loss if I buy and sell multiple shares at different times? Does keeping track of basis really matter?

A. In order to accurately calculate the gain or loss realized on assets you sell, it is important that you keep track of the bases of all of your assets, including stock. However, when it comes to stock--especially lots of stock bought and sold at different times-- it may seem a bit tricky. Fortunately, the rules related to determining the basis of stock sold make the task more manageable.

In general, the basis of stock sold will be determined under one of the following methods: first-in, first-out (FIFO) or specific identification. However, securities held in mutual funds and received as a result as a corporate reorganization may be handled differently.

First-in, first-out (FIFO)

In general, if you buy identical shares of stock at different prices or on different dates and then you sell only part of the stock, your basis and holding period of the shares sold are determined on a first-in first-out (FIFO) basis, based upon the acquisition date of the securities. However, if specific shares sold are adequately identified by the delivery of certificates, by a broker having custody of them, or by a trustee or executor, the basis will be determined by the specific identification method (see below).

The acquisition date for purpose of applying the FIFO method follows the rules for holding period. For example, the acquisition date of securities received by gift takes into account the donor's holding period, and securities received in an estate distribution includes the holding period of the executor or trustee.

Margin accounts. If your shares are held in a margin account, they are considered sold in the order in which they were purchased, rather than the order in which they were placed in the account.

Stock splits or dividends. If you receive shares as a result of a stock split or tax-free stock dividend, they must be allocated among the original lots to which they relate, with the basis of the original shares allocated between the new shares and the old shares based on their fair market values.

Stock rights. If you acquire additional shares by exercising stock rights, your new shares are treated as a separate lot and your basis in them is equal to the amount paid plus the basis of the stock rights.

Multiple contracts. Shares acquired on the same day under several contracts entered into at different times to purchase stock when issued are deemed acquired for the FIFO rule in the same order as the contracts were entered into.

Specific identification

When you are able to identify the securities to be sold, and do so, FIFO will not apply to your basis allocation. The identity of securities sold or otherwise transferred generally is determined by the certificates actually delivered to the transferee (usually by CUSP number). Thus, if you have records showing the cost and holding period of securities represented by separate certificates, you can often better control the amount of gain or loss realized by selecting the certificates to be transferred. But be careful: delivery of the wrong certificates is binding, despite your intention to transfer securities from a different lot.

Example: You hold 1000 shares of IBM. You purchased 400 shares (actually 100 shares that split twice) in 2000 for $8,000 (net brokerage commissions). You bought 400 more shares in 2005 at $18,000; and 200 more in early 2007 for $16,000. You want to sell 300 shares now when its value is down to $50 per share. If you do not specify to your broker before the trade to sell the 200 shares purchased in 2007 and 100 shares from the 2005 lot, you will realize $9,000 in long term capital gains instead of $500 in long-term capital gain and a $6,000 short-term capital loss.

Mutual funds

If you own shares in a mutual fund, you may elect to determine the basis of stock sold or transferred from your accounts by using one of two average cost methods: either the double-category method or the single-category method. An election to use one of the average basis methods for mutual fund shares must be made on either a timely filed income tax return or the first late return for the first tax year to which the election is to apply. Different methods may be used for accounts in different regulated investment companies.

Securities received in reorganization

An exception to the FIFO rule applies to securities received in reorganization (such as a merger) and not adequately identified. These securities are given an average basis, computed by dividing the aggregate basis of the securities surrendered in the exchange by the number of shares received in the exchange. If securities in the same corporation are received in the exchange, however, they are divided into lots corresponding with those of the securities surrendered and the FIFO principle is applied, in the absence of adequate identification on a later disposition.

As illustrated in an example above, there can be negative tax effects from the misidentification of stock sold. If you are uncertain how to properly identify stock sold, please contact the office for further guidance.

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An attractive benefit package is crucial to attract and retain talented workers. However, the expense of such packages can be cost-prohibitive to a small business. Establishing a tax-advantaged cafeteria plan can be an innovative way to provide employees with additional benefits without significantly adding to the cost of your overall benefit program.

Rising healthcare costs affect small businesses

If you are like most employers today, you have been dealing with the sting of rising prices for health benefits for some time. As a matter of economic survival, many small businesses have had to pass on at least some of the cost of providing health, dental and prescription benefits to their employees. As the prices continue to rise to fund these benefits, employees have been required to pay an increasing share of these costs. Establishing a cafeteria plan can be a way to make this problem more palatable for your employees at relatively little cost to your business.

Cafeteria plans defined

Technically, a cafeteria plan is a program through which you can offer your employees a choice between two or more "qualified benefits" and cash. The plan must be set forth in a written document and it can only be offered to employees. Depending on what you want to accomplish through a cafeteria plan, the plan can vary from being extremely simple (e.g., premium conversion plans) to being somewhat more complex as more features are added (e.g. flexible spending accounts).

Premium conversion plans: Popular and simple

A very simple type of cafeteria plan that is very popular among small to mid-size employers is sometimes referred to as a "premium conversion" plan. Establishment of a premium conversion plan would not require you to provide any significant additional funding for benefits other than what you are currently spending.

Here's how it works: through the structure of a cafeteria plan, you can offer your employees the ability to use pre-tax dollars to pay the portion of premiums you require them to contribute for their health, dental, and prescription benefits (including the cost of dependent benefits). Using pre-tax dollars to pay for their portion of health care premiums saves your employees money and will result in more net dollars in their paychecks. It may seem surprising, but your employees will appreciate even this small dollar-saving benefit.

With a premium conversion plan, the only costs to you as an employer is the expense of hiring an attorney or other benefits professional to draft a cafeteria plan document for you and the expense of making the small adjustment to your system of payroll deductions so that the employees' portion of the health benefit premiums is deducted from their gross pay rather than their after-tax pay.

Flexible spending accounts

Another benefit that can be made available under a cafeteria plan is a flexible spending account option. These accounts permit employees to have a specific amount withheld from each paycheck and set aside to be used for reimbursement of medical expenses not covered by the group health insurance plan or to be used to cover dependent care expenses. Keep in mind, however, that if you want to establish flexible spending accounts through a cafeteria plan, it will involve more ongoing administrative expense on your part than a simple premium conversion cafeteria plan.

Additional options

You also may want to offer your employees a cafeteria plan which provides them a set dollar value that each employee can take either as additional salary or choose to spend on a variety of benefits, e.g., health insurance, dental coverage, dependent care, or retirement plan contributions. With this type of plan, all benefits other than additional salary are not taxable to the employee. This type of plan can provide desirable flexibility to your employees, but will also cost more to establish and administer.

As you make the determination regarding what type of benefit program you would like to offer your employees, there are many other options that should be taken into consideration. If you require additional guidance, please contact the office for a consultation.

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An employee stock ownership plan (ESOP) is a retirement plan option that offers even greater tax advantages than many other retirement plans. However, for the small business owner, ESOPs have another significant advantage: in the right situation, an ESOP can be an extraordinarily useful estate and business succession planning tool.

The Internal Revenue Code offers great benefits for tax-qualified retirement plans such as ESOPs. Employers can get a tax deduction for contributions made on employee's behalf to the plan, while employees do not have to pay immediate income tax on these contributions. An employee stock ownership plan (ESOP) is a very specialized type of qualified retirement plan that offers even greater tax advantages than many other retirement plans. However, for the small business owner, ESOPs have another significant advantage: in the right situation, an ESOP can be an extraordinarily useful estate and business succession planning tool.

Inadequate planning can be costly

Unfortunately, it is all too common for owners of closely held businesses to approach retirement age without having an adequate business succession plan in place that will allow them to comfortably retire and enjoy the fruits of their labor. In many cases, these businesses may be very successful but not readily marketable due to heavy dependence on the input from the business owners on an ongoing basis. In these situations, the owner may find it very difficult to sell the business for its full value and due to inadequate planning, may have to sell the business for a fraction of its worth at retirement.

ESOP to the rescue

If you are a business owner considering selling your business at retirement and are concerned about getting the full fair market value for your business, the answer may be right in front of you. In many cases, the most logical buyers for your business may be your key employees. These key employees are familiar with your business including customers, vendors, and processes as well as your long-term vision for the business. They have an excellent chance to continue fostering the success of your business after your departure.

However, in many circumstances, your employees will not have the cash to buy your business outright and therefore, the business must, in one way or another, provide them with the means to pay the purchase price. This is a situation when an ESOP can be used as an effective planning tool to "save the day" by providing a financially effective way to help fund the sale of your business to your key employees at full market value.

Tax benefits are many

There are numerous tax benefits that are available to you as an owner to sell your business to your employees through the use of an ESOP. These benefits allow you t

Sell your shares of stock tax-free to the ESOP;

Utilize an ESOP loan (for which the bank and your company get special tax treatment); and

Have your employees pay for the stock while the business pays back the ESOP loan using (a) deductible and enhanced contributions to the ESOP, and (b) tax deductible dividends.

These benefits mean that by using an ESOP, you can sell your business tax-free and at full value (as determined by an appraiser) to your employees who are more able to pay because they can deduct the purchase price. These tax benefits provide a mechanism for you to receive maximum value for your business in cases where there may not be any other way to accomplish this.

Benefits that keep on giving

Providing business succession to key employees through an ESOP may not only give you adequate funds on which to retire, but also can leave your family with a portfolio of liquid investments in the form of the proceeds from the tax-free stock sale of your stock back to the ESOP, instead of a business that your family may have not know-how to run nor have any desire to run. Further, an ESOP can also help if you have one or more children that want to remain active in the business, while others want to receive an equal share of the your estate and do not want to be required to remain involved in the operation of the business.

Special notes for S Corps

Subchapter S corporations have been permitted to establish an ESOP for the last couple of years. If you are operating as an S corporation and are interested in establishing an ESOP, it is important to be aware of the differences between ESOPs that can be established for standard corporations and S corporations.

An ESOP is an extremely specialized type of profit sharing or stock bonus plan and must comply with all of the requirements for any other tax-qualified retirement plan that are imposed under the Internal Revenue Code and the supporting Treasury regulations. However, an ESOP is only slightly more complicated to establish than a profit sharing or 401(k) plan. For more information about how an ESOP can be used in your business succession plans, please contact the office to schedule a consultation.

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Incentive stock options (ISOs) give employees a "piece of the action" while allowing employers to attract workers at relatively inexpensive costs. However, before you accept that job offer, there are some intricate rules regarding the taxation of ISOs that you should understand.

ISOs give employees a "piece of the action" while allowing employers to attract workers at relatively inexpensive costs. However, before you accept that job offer, there are some intricate rules regarding the taxation of ISOs that you should understand.

How are ISOs taxed?

An incentive stock option is an option granted to you as an employee which gives you the right to purchase the stock of your employer without realizing income either when the option is granted or when it is exercised. You are first taxed when you sell or otherwise dispose of the option stock. You then have capital gain equal to the sale proceeds minus the option price, provided that the holding period requirement is met.

Note. The IRS has temporarily suspended collection of ISO alternative minimum tax (AMT) liabilities through September 30, 2008.

How long do I need to hold ISOs to get capital gain treatment?

To obtain favorable tax treatment, the stock acquired under an incentive stock option qualifies for favorable long-term capital gain tax treatment only if it is not disposed of before the later of two years from the date of the grant of the option, or one year from the date of the exercise of the option. If this holding period is not satisfied, the portion of the gain equal to the difference between the fair market value (FMV) of the stock at the time of exercise and the option price is taxed as compensation income rather than capital gain. In this case, you may be subject to the higher rate of income imposed on ordinary income.

For example, your employer granted you an incentive stock option on April 1, 2006, and you exercised the option on October 1, 2006, you must not sell the stock until April 1, 2008, to obtain favorable tax treatment (the later of two years from the date of the grant or one year from the date of exercise).

What key dates should I remember?

Because of the importance of receiving capital gain treatment, it is important that you keep in mind key dates such as the date of grant of the ISO and its date of exercise. These periods are measured from the date on which all acts necessary to grant the option or exercise the option have been completed. Therefore, the date of grant is treated as the date on which the board of directors or the stock option committee completes the corporate action which constitutes an offer of stock, rather than the date on which the option agreement is prepared. The date of exercise is the date on which the corporation receives notice of the exercise of the option and payment for the stock, rather than the date the shares of stock are actually transferred.

Will I be subject to alternative minimum tax?

The effect of the alternative minimum tax (AMT) on ISOs can amount to a potential trap for the unwary. This is because under the regular tax there is no tax until the stock is sold or otherwise disposed of. Under the AMT, however, the trap takes place when the ISO is exercised, since alternative minimum taxable income includes the difference between the FMV of the stock on the date the ISO is exercised and the price paid for the stock (the "ISO spread").

If you pay AMT, you are given a credit against regular income tax for the portion of the AMT attributable to ISOs and other tax preference items that result in deferral of income tax. The credit is taken in later years when no AMT is due, and may be taken to the extent that regular tax liability exceeds tentative minimum tax liability. The effect of this is that the AMT is a prepayment of tax, rather than an additional tax.

Since the AMT only applies if it is higher than your regular income tax, one strategy is to time the exercise of ISOs each year to come under the AMT exemption levels. Purely from a tax standpoint, the ideal situation is to exercise ISOs each year that would result in AMT equal to your regular tax. Of course, other factors, such as market conditions, financial needs, etc. may play a greater role in deciding when to exercise an option. If you pay high property tax or state income tax, you may find it more challenging to calculate the optimum exercise of ISOs in relation to the AMT, since both of these deductions are counted against their annual AMT exemption.

ISOs can be a nice additional employee benefit when considering a job offer. However, because the tax implications surrounding certain key trigger events related to ISOs can have a significant impact on your tax liability, we suggest that you contact the office for additional guidance.

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