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Reporting Company Stock Sales
2016 UPDATES!
  
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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 NEW! Tax Returns quiz and its study guide in the answer key.

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 podcast on tax return tips and how to avoid reporting mistakes!

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


  Articles   FAQs  

How To Avoid Paying Too Much Tax: Understanding The Revised Form 1099-B And Form 8949 For Reporting Stock Sales On Your Tax Return This is premium content

Bruce Brumberg
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

myStockOptions Tax Team
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: 8:06.

Restricted Stock & RSUs: 10 Tax-Return Mistakes To Avoid This is premium content

The myStockOptions.com Tax Team
UPDATES! The 2016 tax season has the potential to be confusing if you sold stock in 2015. This article explains common errors to avoid when reporting stock sales on your tax return and provides helpful guidance on various other tax topics involving restricted stock and restricted stock units.

12 Tax-Return Mistakes To Avoid With Stock Options And ESPPs

Bruce Brumberg and Lynnette Khalfani
UPDATES! The 2016 tax season has the potential to be confusing if you sold stock in 2015. This article explains common errors to avoid when reporting stock sales on your tax return and provides helpful guidance on various other tax topics involving stock options and ESPPs.

IRS Form 3922 For ESPPs: What You Need To Know, And How It Can Help You Understand ESPP Taxation This is premium content

Bruce Brumberg
Stock purchases made through an ESPP during a calendar year are reported to you and the IRS on Form 3922 early in the following year. This article explains what you need to know about the information on the form, and how the form can help you better understand the complexities of ESPP taxation.

IRS Form 3921 For Incentive Stock Options: What You Need To Know, And How It Can Help You Understand ISO Taxation This is premium content

Bruce Brumberg
Incentive stock option (ISO) exercises made during a calendar year are reported to you and the IRS on Form 3921 early in the following year. This article explains what you need to know about the information on the form, and how the form can help you better understand the complexities of ISO taxation.

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

Tom Davison and William Whitaker
Notable shifts in tax rates have occurred for people with high incomes. Part 1 surveys these important tax changes and considers their impact on planning.

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

Tom Davison and William Whitaker
Notable shifts in tax rates have occurred for people with high incomes. Part 2 looks at planning strategies involving capital gains rates, the AMT, and ISOs, and considers general ideas related to income-shifting.

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

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

Alan B. Ungar
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.

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NEW! What are the top 10 questions I should ask about the reporting of stock sales on my tax return?

This FAQ presents 10 questions you should ask to be sure that you report your stock sales accurately and avoid costly mistakes that attract the attention of the IRS...

UPDATES! What's new for tax-return season?

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

UPDATES! 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 I acquired by stock option exercise, restricted stock vesting, or ESPP purchase? This is premium content

Form 1099-B or the equivalent substitute statement is necessary for the accurate completion of your tax return....

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?

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 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 all too easy to make costly tax-return errors that attract unwanted IRS attention. Learn how to prevent mistakes...

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...

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...

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...

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