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Annotated diagram of Schedule DTax errors can be costly! Don't draw unwanted attention from the IRS. Our Tax Center explains and illustrates the tax rules for sales of company stock, W-2s, withholding, estimated taxes, AMT, and more.



ISOs

Incentive stock options carry great potential tax benefits, but their taxation can be complex, especially when the alternative minimum tax comes into play. Browse an overview of this section below, or explore the subtopics to the left. See also the ISO sections of the Tax Center.

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Stock Option Financial Planning After Your Tax Return Is Filed And At Year-End (Part 1) This is premium content

Tom Davison and Liam Hurley
UPDATED FOR 2013! The time right after you have completed your tax return is ideal for big-picture financial planning. You can more accurately project your income and likely tax situation for the remainder of this year and the next, including AMT risk and capital-loss carry-forwards, to develop your strategy.

New Tax Act And Medicare Surtax: Impact On Stock Option And Restricted Stock Strategies This is premium content

Alan B. Ungar
NEW! The American Taxpayer Relief Act and the Affordable Care Act introduced tax-rate increases you need to consider in deciding when to exercise stock options, when to sell company stock, and how to plan around income from restricted stock vesting. This article explains the changes in tax law and suggests strategies for minimizing the new taxes.

The Alternative Minimum Tax Sweet Spot: Planning Opportunities This is premium content

Tom Davison and William Whitaker
NEW! "My income is around half a million dollars, and I'm paying the alternative minimum tax. It's annoying, and I feel trapped. Now what?" Surprisingly, the best move may be to increase income, and pay even more alternative minimum tax! Find out why by reading this intriguing article.

The ISO Tax Trap And The AMT Credit Myth: What To Do Before Exercise And At Year-End This is premium content

Alan Ungar
The tax reductions of the past few years have brought both good and bad news for holders of incentive stock options. While you may have lower capital gains rates when you hold the shares long enough after exercise, it is harder to avoid the risks of the alternative minimum tax (AMT) and to fully recover any AMT credit.

The Refundable AMT Credit: How It Works & What You Need To Know This is premium content

Bruce Brumberg and Matt Simon
Until fairly recently, alternative minimum tax (AMT) credits could be applied against your tax bill only in years when your regular tax liability exceeded your AMT liability. However, Congress now allows a faster rate for using AMT credits that are more than three years old. This article explains what you need to know about this "refundable" AMT credit, which is available through tax year 2012 (returns filed in 2013).

Refundable AMT Credit: Different Rules For Old Unused Credit

Kaye A. Thomas
Special rules for old unused AMT credits, first available in 2007, were drastically revised for the tax years 2008 through 2012. This is the first of two articles on the refundable AMT credit, which provides a way for many people to use more AMT credits than they could under the regular rules.

Refundable AMT Credit: The Calculation

Kaye A. Thomas
Special rules for old unused AMT credits, first available in 2007, were drastically revised for the tax years 2008 through 2012. This is the second of two articles on the refundable AMT credit, which provides a way for many people to use more AMT credits than they could under the regular rules.

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.

Early-Exercise ISOs Complicated By Final IRS Regulations This is premium content

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

Taking An Overseas Assignment: Stock Compensation For Mobile Employees (Part 1) This is premium content

Mark Miller
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.

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UPDATED FOR 2013! What are the biggest mistakes related to stock options I can make on my tax return, and how can I avoid them? This is premium content

It is easy to make tax return mistakes that lead to paying more than necessary or (perhaps worse) an IRS review. This tax season in particular will be more confusing than most because of the new Form 1099-B, the new Form 8949, and the significantly revised Schedule D...

Form 8949 and Sch. D diagrams! After I have met the ISO holding periods, how do I report a sale on my tax return? This is premium content

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

Form 8949 and Sch. D diagrams! I did a cashless exercise with my incentive stock options. Should I still report it on Form 8949 and Schedule D even though the gain is zero? And what about the alternative minimum tax? This is premium content

By selling the ISO stock when you exercised it, you eliminated the spread at exercise from the...

Form 8949 and Sch. D diagrams! How do I report a sale of shares in an ISO sell-to-cover exercise? This is premium content

To report the sale of shares in a sell-to-cover exercise, you complete Form 8949 along with Schedule D for the year of...

Form 8949 and Sch. D diagrams! 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? This is premium content

The rules are similar to those that apply to sales of ISO shares made in the same year as exercise; however, the difference is...

Form 8949 and Sch. D diagrams! 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 was higher or lower than at exercise? This is premium content

The calculation of the amount of ordinary income and capital gain/loss will vary according to the...

Form 8949 and Sch. D diagrams! When I sell my ISO shares 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 Form 8949 and Schedule D? This is premium content

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

UPDATED! What are the big changes with reporting stock sales on my tax return? Why have these changes occurred?

Major changes in the tax reporting and filing for stock sales became effective in 2012 (i.e. starting with stock sales made in 2011). The revised reporting and filing rules now apply every tax season...

UPDATED! How has IRS Form 1099-B changed for sales of stock acquired from my stock options, restricted stock, or ESPP? This is premium content

Your brokerage firm issues IRS Form 1099-B by mid-February in the year following the year of sale. Form 1099-B is an important document that you must have to complete your tax return...

NEW! In the cost basis I use to report sales of company stock on my tax return, what part comprises the W-2 income from stock compensation or an ESPP? This is premium content

When your W-2 income is added to the price you paid for the stock, this is your cost basis on your tax return. The table below presents the compensation portion of your tax basis for all types of stock grants and ESPPs...

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