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NEW! Six Ways Tax Reform Affects Your Stock Compensation And Financial Planning

Effective from the start of 2018, the Tax Cuts & Jobs Act includes provisions that either directly or indirectly affect stock compensation, whether in financial planning or in stock plan administration (though the core tax treatments have not changed). This article details six provisions that have an impact on the taxation of stock compensation or holdings of company shares.

UPDATES! The Impact Of Tax-Law Changes On Stock Option And Restricted Stock Strategies This is premium content

Podcast included! While in 2018 Tax Cuts & Jobs Act superseded many prior tax provisions, other tax provisions introduced in previous legislation (such as the Affordable Care Act, i.e. Obamacare) remain in place. Income thresholds for the tax brackets trigger higher tax rates, so it is wise to monitor the tax impact of income-generating events stemming from stock compensation. This article suggests strategies for minimizing their impact.

NEW! Private Company Stock Options And RSUs: 10 Facts To Know About The New Tax-Deferral Opportunity This is premium content

Stock options and RSUs are popular at startups and late-stage pre-IPO companies. However, shares in privately held companies typically lack liquidity and thus cannot be sold, creating difficulty when taxes are owed on the income recognized. To address this problem, the Tax Cuts & Jobs Act introduced an income-deferral opportunity for certain types of stock compensation at privately held companies in Section 83(i) of the tax code.
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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.

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.

UPDATES! Tax Planning For Options, Restricted Stock, And ESPPs Affected By The 2013 Tax-Law Changes (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 ongoing impact on planning. Even after the changes made by the Tax Cuts & Jobs Act in 2018, many of the rates and income thresholds covered in this article still apply.

Tax Planning For Options, Restricted Stock, And ESPPs Affected By The 2013 Tax-Law Changes (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.

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

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...

UPDATES! How does Obamacare continue to affect 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 about legislation affecting the alternative minimum tax?

The Tax Cuts & Jobs Act, which took effect in 2018, made significant changes to factors in the calculation of the alternative minimum tax (AMT) that will generally reduce the likelihood of...
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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? What key facts should I know about it? 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...

NEW! How does tax reform affect stock compensation?

In effect from the start of 2018, the Tax Cuts & Jobs Act has provisions that directly and indirectly affect stock compensation...

NEW! Did tax reform change the tax-withholding rates on stock compensation? This is premium content

Yes. The Tax Cuts & Jobs Act, which took effect at the start of 2018, changed the withholding rates...

NEW! How does tax reform affect restricted stock and RSUs? This is premium content

While the core tax treatment of restricted stock and RSUs has not changed, the Tax Cuts & Jobs Act has provisions that directly and indirectly affect restricted stock/RSUs...

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...

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? This is premium content

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...

How did the American Taxpayer Relief Act affect stock compensation?

Before the Tax Cuts & Jobs Act, whick took effect at the start of 2018, the previous big tax legislation was the American Taxpayer Relief Act...

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...