ISOs: Taxes Advanced

How Tax Rate Changes Impact Your Stock Grant Strategies (Part 3): Incentive Stock Options

Stanley Trotta with Robert Gordon
President Obama's proposals will probably raise taxes after 2010. Should you take action with stock options ow or wait until new rates apply? Part 3 looks at incentive stock options.

Stockbrokers' Secrets (Part 7): Year-End Planning For ISOs

W.E.B. Bantling and Michael Beriss
UPDATED FOR 2009! Learn about year-end planning specifically for incentive stock options, including ideas related to the alternative minimum tax.

How To Report Sales Of Company Stock

The myStockOptions.com Tax Team
UPDATED FOR 2009! Learn how to report your sales of company stock on Schedule D of IRS Form 1040. Our comprehensive guide to Schedule D reporting covers sales of stock from nonqualified stock options, incentive stock options, restricted stock, restricted stock units, performance shares, employee stock purchase plans, and stock appreciation rights.

Avoid Tax Return Mistakes With Stock Options & ESPPs: What You Need To Know In 2009

Bruce Brumberg and Lynnette Khalfani
Tax returns can be onerous. Read this article if you are puzzled by Form 1099-B or don't know how and where to report sales of company stock from options or employee stock purchase plans.

Stock Option Fundamentals (Part 5): Incentive Stock Option Taxation & Alternative Minimum Tax

Marilyn Renninger
You're ready to delve deeper into how and when different taxes apply to ISOs, including the AMT. You need to consider taxes at exercise and at sale to put together a strategy that maximizes the value of your options.

ISOs And Wash Sales: A Trap Within A Trap

Kaye Thomas
A trap awaits those who, after selling shares from exercised ISOs to avoid AMT, want to buy back the stock.

Taking An Overseas Assignment: Stock Compensation For Mobile Employees (Part 1)

Mark Miller
UPDATED! For employees and executives, international travel and relocation are increasingly common. The taxation of "mobile employees" is always complex, and never more than with equity compensation. Part 1 introduces the key concepts and rules, including the sourcing and apportioning of income.

Taking An Overseas Assignment: Stock Compensation For Mobile Employees (Part 2)

Mark Miller
International assignments or relocations can present attractive opportunities for career advancement. However, the taxation of equity compensation for mobile employees raises complex issues. Part 2 looks at specific scenarios, withholding taxes, and tax equalization.

Hedging Your ISO Stock

Robert Gordon and Charlotte Lyman
Hedging stock from exercises of incentive stock options (ISOs) is complex, but it is possible in certain situations. Financial engineering can create a floor under the ISO stock while letting the capital gains holding period continue.

Final ISO Regulations Affect Stock Plan Design, Optionholders, And Advisors (Part 1)

Ellie Kehmeier and Elizabeth Drigotas
The final rules clarify and consolidate a tangle of proposed, temporary, and final regulations, as well as other guidance, that governed the taxation of ISOs, including rules for disqualifying dispositions.

Final ISO Regulations Affect Stock Plan Design, Optionholders, And Advisors (Part 2)

Ellie Kehmeier and Elizabeth Drigotas
The final rules clarify and consolidate a tangle of proposed, temporary, and final regulations, as well as other guidance, that governed the taxation of ISOs, including rules for the $100,000 ISO limit.

Early Exercise ISOs Complicated By Final IRS Regulations

Michael Frank
The IRS has issued final regulations on ISOs. Understand how these final regulations increase the risks of early exercise.

Now Is The Time To Exercise ISOs

Robert Gordon
Investment News
Before the end of the year, review any ISO stock you're holding from earlier exercises and consider strategies for the following year.

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The amount of my spread at exercise was not listed on the W-2 that I received from my company, even though I made a disqualifying disposition. Do I report this gain on my tax return, and how will I be taxed?

This type of situation, in which the disqualifying disposition does not appear on the W-2, is more likely to occur when...

NEW! Even though no withholding is required for ISOs, can I still pay the federal and state taxes when I make a cashless exercise?

While some companies might permit this if asked, the IRS may not allow the practice. The situation is far from clear, as the tax code...

Schedule D diagram! After I satisfy the ISO holding periods, how do I report a sale on my tax return?

After you have held the stock more than two years from grant and one year from exercise, the spread between the sales and exercise prices is...

Schedule D diagram! I did a cashless exercise with my incentive stock options (ISOs). Should I report the transaction for capital gains purposes on Schedule D even though the gain is zero, and should I worry about the alternative minimum tax (AMT)?

By selling the ISO stock at the same time you exercised it, you eliminated the AMT. The same would be true if you had sold the stock at...

Schedule D diagram! How am I taxed if I have made a disqualifying disposition (e.g., sale) of ISO shares in a different year than the year I exercised the option? How do I report this?

The rules are similar to those that apply to sales of ISO shares made in the same year as exercise; the difference is that you are taxed in the year of the sale of the stock...

Schedule D diagram! I exercised my ISOs and sold the ISO stock later in the same year. How is this reported on my tax return when the stock price at sale is higher or lower than at exercise?

If you sold the stock at a price higher than it was on the day of your exercise, the spread at exercise is still...

Schedule D diagram! When I sell my ISO stock in a disqualifying disposition, will the broker's commission reduce the amount of ordinary income on my W-2 or the amount of gross sales proceeds on my Schedule D?

The final IRS/Treasury regulations on ISOs make clear that the amount of ordinary income in a disqualifying disposition is...

I acquired stock from exercises and restricted stock vesting a few years ago. When I sell the stock, how do I rediscover the cost basis for Schedule D of my tax return?

Let's first review the tax rules and the W-2 reporting. The tax basis for...

UPDATED! My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return?

A casualty or theft loss would allow you to deduct the lost amount against your ordinary income, subject to some limits. However, Treasury regulations and court rulings would probably stand in your way. Nevertheless, what you can do is...

In what ways can I pay my taxes if I don't have the money to pay them with my tax return?

Apart from applying for an extension, which delays only the filing of your tax return, not the actual payment, you have a few choices...

How do I use stock that I own to exercise an option in a stock swap? What is the tax treatment?

A "stock swap" or "stock for stock" exercise is a stock option exercise in which the exercise price is paid with shares of company stock you own...

Can I use ISO stock to exercise NQSOs? Is this a disqualifying disposition that eliminates the special tax treatment for ISOs?

Yes, you can use ISO stock to exercise NQSOs without disqualifying it, as the...

UPDATED FOR 2009! What are some year-end strategies for stock options and restricted stock?

This depends on your financial situation, on whether your decisions should be entirely tax-driven, on what you did earlier in the year, on your outlook for your company's stock price, and on the prospects for changes in tax law during the year ahead. Below we present 10 ideas...

What is the tax impact on me if my company modifies outstanding stock options or SARs, such as by extending the option term?

With approval from the board, and perhaps also shareholders, your company can modify outstanding grants in a way that is consistent with its stock plan. However, it should avoid tax pitfalls for you and the company, such as...

Is the gifting or donation of stock that I acquired from an ISO exercise or ESPP purchase a disqualifying disposition? What is the tax treatment for early sale?

A disqualifying disposition occurs if you sell, transfer, exchange, gift, or donate the stock that you acquired without...

Both dividends and long-term capital gains are now taxed at the same rate. Can I net my dividends from my company stock against capital loss from the sale of company stock or another security?

No. Under the 2003 tax cut, qualified dividends are taxed at the same rates as long-term capital gains...

The spread on my cashless ISO exercise is reported on my W-2 as ordinary income. Can I use my stock-trading losses to offset this income?

The tax law says that you can offset losses against only the same type of income...

Is all the income that results from a disqualifying disposition of ISO shares a short-term capital gain that I can net against my capital losses on Schedule D of my tax return?

No. All or part of it may be ordinary income. You have capital gains only when you...

My company backdated more stock options than just those of the senior executives. How does this affect employees like me and the taxation of my stock grants?

At a minimum, do not expect any new stock option grants with an exercise price lower than the market price on the grant date. The tax treatment varies by type of grant. Some of the companies involved in the controversial backdating of stock options restricted employees from...

If I sold my stock immediately upon exercise or at vesting, the transaction would violate the insider-trading laws and the laws of short-swing profits under Section 16(b) because I had a purchase within six months of the sale. Would this then delay the date of the tax treatment?

The spread at exercise is what matters for the tax calculation...

Is writing call options on, or buying put options for, my ISO stock a disqualifying disposition?

The put options you buy give you the right to sell the stock at a price you choose. With call options you are selling the right to someone else to "call away" the stock you own. The IRS ruled that the...

What happens if I live in state A when my stock options are granted, state B when I perform some of my services, state C when I exercise the options, and state D when I sell the shares?

Generally, each state you live in determines what income is taxable and when. For administrative ease, many companies...

If I move to another country to work, will I still have to pay US taxes on option exercises, restricted stock vesting, and stock sales? Can I avoid double taxation?

The United States taxes the worldwide income of US citizens regardless of whether the income arises from activities in the US. In addition, the other country may impose taxes too. But the US has tax treaties with certain nations to help taxpayers avoid double taxation...

What is the tax treatment of ISOs after death?

ISOs are treated more favorably then NQSOs. For estate-tax purposes it's the same, but at...

I exercised ISOs and am hoping to wait 12 months before selling to get the favorable ISO tax treatment. What happens in a cash M&A deal when I'm trying for the one-year holding-period mark but the buyer pays cash for the stock? Is there any way around incurring a disqualifying disposition?

If, as is normally the case, you have no power to refuse or delay your stock sale, no exception...

Does the accelerated vesting of my stock options, restricted stock, and/or performance shares in a change of control or termination have any tax impact on me, such as for ISOs and golden parachute payments?

With stock grants of normal size, you face no tax impact beyond the standard tax treatment. ISOs may be converted to NQSOs should any acceleration of vesting cause...

Will my company be able to take a tax deduction for the value of my restricted stock, restricted stock units, performance shares, or stock options if my compensation already exceeds $1 million?

This depends on what triggers vesting. Section 162(m) of the tax code limits your company's deduction to $1 million unless a senior officer's compensation over this amount meets the performance-based exception. Stock grants are structured to meet this by...

UPDATED! Does the American Jobs Creation Act, particularly Section 409A on deferred compensation, affect my stock grants?

A number of tax law provisions and interpretations that may affect your stock grants occur in the wide-ranging American Jobs Creation Act (AJCA); the final regulations on deferred compensation under Section 409A, which adopt the...

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