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Tax Center

As featured in WebCPA and Plansponsor, our Tax Center teaches the withholding, reporting, and filing rules for stock options, ESPPs, restricted stock, and SARs. Browse a section overview below, or explore the subtopics to the left.

Test Your Knowledge Test and improve your knowledge with our Taxes quiz and its study guide in the answer key.

Want to know more? Listen to our updated podcast on tax return tips and how to avoid reporting mistakes!

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


  Articles   FAQs  

VIDEO! Restricted Stock & RSUs (Part 2): Taxes And Related Key Decisions

Bruce Brumberg
Presented by the editor-in-chief of myStockOptions.com, this engaging video covers the basic tax treatment of restricted stock and restricted stock units (RSUs), including the tax rates, the timing of taxation, and withholding. Running time: 3:57

Tax Planning For Options, Restricted Stock, And ESPPs After 2013 Tax Law Changes: High-Income Taxpayers Impacted Most (Part 1)

Tom Davison and William Whitaker
The beginning of 2013 brought notable shifts in tax rates for people at higher income levels. Part 1 surveys the important tax changes and considers their impact on planning.

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

Tom Davison and William Whitaker
The beginning of 2013 brought notable changes in tax rates for people at higher income levels. Part 2 looks at planning strategies involving capital gains rates, the AMT, and ISOs, and considers general ideas related to income-shifting.

ESPP Taxation Made Simple This is premium content

Matt Simon
Your employee stock purchase plan may be one of the best benefits offered by your company. However, to appreciate the advantages of enrolling in the ESPP you must understand the tax consequences of participation. This article explains the tax basics.

Restricted Stock Units Made Simple (Part 2): Taxation This is premium content

Matt Simon
The taxation of RSUs generally resembles that of restricted stock but carries some important differences.

Decisions At Grant With Restricted Stock (Part 1): Tax Fundamentals This is premium content

Tom Davison
Thanks to the IRS, with restricted stock you have to make decisions immediately at grant. Learn the rules that accompany this increasingly popular type of equity compensation.

Fundamentals Of Employee Stock Purchase Plans (Part 3): Tax Treatment Of Your Purchases And Sales This is premium content

Alisa Baker
Now let's look at the employee tax issues associated with employee stock purchase plans (ESPPs). ESPP tax rules can be more confusing and less logical than those that govern stock options.

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

Alan B. Ungar
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.

Fundamentals Of Employee Stock Purchase Plans (Part 4): Down Markets And Other Tax Topics This is premium content

Alisa Baker
In Part 4 we consider the taxation of employee stock purchase plans (ESPPs) that are not qualified under Section 423, and the tax issues of down markets, death, and withholding.

Stock Option Fundamentals (Part 4): NQSO Taxation This is premium content

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

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UPDATES! 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

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...

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

The new Form 8949 is where you now list the details of each stock sale on your tax return, while the revised Schedule D is where you now merely aggregate the column totals from Form 8949 to report your total long-term and short-term gains and losses. From our interpretation of the forms and their instructions, myStockOptions.com recommends the following reporting steps to avoid overpaying taxes...

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...

W-2 diagram! What will my W-2 show after I exercise nonqualified stock options? This is premium content

The gain from your nonqualified stock option exercise(s) is totaled on the W-2 with other income in the following boxes...

W-2 diagram! How is an NQSO stock-swap exercise reported on my W-2? This is premium content

Your W-2 totals the full gain from your NQSO exercise with your other income in the following boxes...

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...

What should I do if I don't receive a W-2 or if I lose it? This is premium content

If the company has not issued a W-2 by the middle of February, the IRS suggests...

UPDATES! What tax statement will I receive from my broker after a sale of company stock I acquired by stock option exercise, restricted stock vesting, or ESPP purchase? This is premium content

You will need to gather certain information to complete your tax return. The broker will send you IRS Form 1099-B for the proceeds...

After I exercise NQSOs, will I need to make estimated tax payments? This is premium content

At a minimum, when you exercise your stock options, your company will withhold taxes at the required federal withholding rate for supplemental income. However, depending on your income, this minimum withholding may not be enough. If so, you will need to...

Are there any strategies for paying estimated taxes on income from stock options and restricted stock? This is premium content

Estimated-tax periods end on the last days of March, May, August, and December, with payments due by the 15th (or the next business day) of the following month. If you are paying estimated taxes, one strategy is that just after the start of an estimated-tax period you can...

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