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Check out our podcast and video on the tax forms and reporting rules for stock sales.

Articles

UPDATES! How The Trump Presidency And Tax Reform May Affect Stock Compensation

Potential tax changes under the Republican president and the Republican-controlled Congress may have a meaningful impact on stock compensation and employee ownership.

Tax Planning For Options, Restricted Stock, And ESPPs After The 2013 Tax-Law Changes: High-Income Taxpayers Impacted Most (Part 2) This is premium content

Part 2 of this article series looks at planning strategies involving capital gains rates, the AMT, and ISOs, and considers general ideas related to income-shifting.

UPDATES! American Taxpayer Relief Act And Medicare Surtax: Impact On Stock Option And Restricted Stock Strategies This is premium content

Podcast included! The American Taxpayer Relief Act and the Affordable Care Act introduced tax-rate increases you must consider in deciding when to exercise stock options, when to sell company shares, and how to plan around income from restricted stock/RSU vesting. Although tax reform is on the horizon, these tax laws will remain in place until new laws are adopted.
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Avoid Overpaying Tax On Stock Sales: Understand Forms 1099-B And 8949 For Tax-Return Reporting This is premium content

UPDATES! The stock-sale information provided by brokers on IRS Form 1099-B has changed. Cost-basis reporting, both for your broker on Form 1099-B and for you on your tax return, is now more complex, confusing, and vulnerable to errors. This article explains the crucial facts you must know to avoid overpaying tax or attracting unwanted IRS attention.

UPDATES! Tax Planning For Options, Restricted Stock, And ESPPs After The 2013 Tax-Law Changes: High-Income Taxpayers Impacted Most (Part 1) This is premium content

Notable shifts in tax rates occurred in 2013 for people with high incomes. Part 1 surveys these important tax changes and considers their impact on planning. Unless or until tax reforms become effective, the rates and income thresholds covered in this article still apply.

VIDEO! Tax-Return Reporting Of Company Stock Sales: How To Avoid Overpaying Taxes

Learn the rules for reporting stock sales on your tax return, along with costly errors to avoid if the shares you sold came from stock options, restricted stock/RSUs, stock appreciation rights, or an employee stock purchase plan. Among other issues, you must understand your "cost basis" to avoid overpaying your taxes. Running time: 8:05.

VIDEO! Tax-Return Forms And Reporting Rules For Stock Sales

Learn how to prevent costly tax return mistakes with this animated presentation on IRS Form 1099-B, IRS Form 8949, and Schedule D.

IRS Publication 550: Investment Income And Expenses

This extensive IRS guide covers many topics related to reporting income and expenses from investments, including dividends (Chapter 1), capital gains (Chapter 4), and interest on loans (Chapter 3).

IRS Guide To Auditing Techniques For Stock-Based Compensation

The IRS tips its hand on what its agents look for in audits related to all types of stock pay to ensure compliance, whether by corporations or executives.

FAQs

NEW! How might tax reform affect stock compensation?

The tax-reform principles proposed by the Trump administration would, if converted into law, affect stock compensation in a few ways...

NEW! How would the repeal of Obamacare affect stock compensation? This is premium content

The repeal of the Affordable Care Act (Obamacare) to make way for new health-care legislation would impact the tax treatment of stock compensation in a few ways...

UPDATES! What are capital gains and capital losses? What are the capital gains tax rates?

Capital gain is income that arises from the sale of a capital asset. Gain from the sale of securities held for investment, such as shares acquired from stock compensation...
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What tax changes under the American Taxpayer Relief Act affect stock compensation?

The following changes in tax rates apply to ordinary income triggered by stock option exercises, restricted stock and RSU vesting, and ESPP purchases...

UPDATES! How have recent tax laws changed the withholding taxes on my equity compensation? This is premium content

Tax rates for people in the highest ordinary income brackets rose under the American Taxpayer Relief Act and the Affordable Care Act. The table in this FAQ outlines the income levels that trigger changes in the withholding of federal and FICA taxes...

UPDATES! How does Obamacare affect my Medicare tax and stock compensation planning? This is premium content

Two features in the Affordable Care Act affect your Medicare tax and any planning to minimize it. For people whose yearly income is above certain thresholds, the Medicare tax on both compensation and investment income increased in 2013, when...

What is the latest news from Congress about legislation relating to the alternative minimum tax?

The American Taxpayer Relief Act has three provisions on the alternative minimum tax (AMT) that are important for high-income taxpayers, particularly those who exercise incentive stock options...

Has the likelihood of a tax audit increased? This is premium content

Yes, substantially. In addition, fluctuations of income, which can be caused by stock compensation, are a red flag that can trigger an audit. According to research...

What's new for tax-return season?

Here's a quick take on issues to be aware of when preparing your federal tax return...

What are some major issues to be aware of when reporting stock sales on my tax return? Why have these issues arisen?

Major changes have occurred in the tax reporting for stock sales during the past few years, making accurate tax-return reporting more complex and difficult...

What tax statement will I receive from my broker after a sale of company stock? This is premium content

Form 1099-B or the equivalent substitute statement is necessary for the accurate completion of your tax return. Five facts you must know about this reporting to avoid tax-return mistakes are...

How have IRS Form 1099-B and cost-basis reporting changed for sales of stock acquired from my stock options, restricted stock, or ESPP? What do I need to do differently because of the changes?

If you sold shares during the calendar year, your brokerage firm will issue IRS Form 1099-B by mid-February of the following year. This is an important document that you must have to complete your tax return for the year of sale...

What if the wrong cost basis is reported on my 1099-B? How do I report the right cost basis on Form 8949 of my tax return? This is premium content

From our interpretation of the forms and their instructions, myStockOptions.com recommends the following reporting steps to avoid overpaying taxes...