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How To Report Sales Of Company Stock On Your Tax Return

The myStockOptions.com Tax Team
Learn how to report sales of stock on your tax return. Annotated diagrams of Form 8949 and Schedule D help you make sense of the reporting rules.

Restricted Stock & RSUs: What You Must Know To Avoid Tax-Return Mistakes This is premium content

The myStockOptions.com Tax Team
The 2014 tax-return season has the potential to be more confusing than most if you sold stock in 2013. Read this article for tips on crucial topics relating to restricted stock and restricted stock units.

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

Bruce Brumberg
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.

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
NEW! 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.

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.

Restricted Stock: Tax, Financial, Estate, And Retirement Planning (Part 2) This is premium content

Richard Friedman
Careful planning can help you maximize the value of restricted stock and RSUs by preparing you for decisions you must make. Part 2 covers complex issues in financial, estate, and retirement planning.

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

Mark Miller
Overseas travel and relocation are increasingly common, but the taxation of internationally mobile employees is complex. Part 1 introduces the key cross-border topics you must know about equity compensation, including the sourcing and apportioning of income.

Taking An Overseas Assignment: Stock Compensation For Mobile Employees (Part 2) This is premium content

Mark Miller
International assignments or relocations can present attractive opportunities for career advancement. However, the taxation of equity compensation for mobile employees raises complex issues. Part 2 looks at specific scenarios, withholding taxes, and tax equalization.

Decisions At Grant With Restricted Stock (Part 3): Analyze Your Alternatives This is premium content

Tom Davison
Now that you understand the risks of choosing to be taxed at grant with a Section 83(b) election, should you do it? Part 3 takes you through the analysis.

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

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

How Tax Rate Changes Impact Your Stock Grant Strategies (Part 2): Restricted Stock This is premium content

Stanley Trotta with Robert Gordon
With tax increases in mind, now may be a good time to re-evaluate your current financial-planning strategy for equity compensation and company stock holdings to determine whether action is required. Part 2 looks at restricted stock and restricted stock units.

Year-End Strategies For Restricted Stock: Ideas To Consider This is premium content

Bruce Brumberg
UPDATED FOR 2013! As part of your year-end and year-beginning tax planning, don't forget to review your holdings in restricted stock, performance shares, and other company stock you may own. This article presents strategies that many experts suggest.

Stockbrokers' Secrets (Part 3): Year-End Planning For NQSOs, Restricted Stock, And RSUs This is premium content

W.E.B. Bantling and Michael Beriss
UPDATED FOR 2013! Learn about year-end ideas that apply to NQSOs and restricted stock/RSUs, and consider the impact of tax-rate changes that became effective in 2013.

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What are the biggest mistakes with restricted stock or RSUs that I can make on my tax return, and how can I avoid them? This is premium content

It is all too easy to make tax-return errors that lead to paying more than necessary or (perhaps worse) an IRS review. Learn how to prevent expensive mistakes...

What are the big changes in 2014 with reporting stock sales on my tax return? Why have these changes occurred?

Major changes have occurred in the tax reporting and filing for stock sales during the past few years, making accurate 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

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

Form 8949 and Sch. D diagrams! How do I report a sale of restricted stock on my federal income-tax return? This is premium content

You need to complete Form 8949 and Schedule D for the year when you sold your stock and file them with your Form 1040 federal income-tax return. You do this even if...

Form 8949 and Sch. D diagrams! Do I need to report on my tax return the restricted stock I sold or surrendered to my company for the tax withholding? This is premium content

You should definitely report a sale for taxes at vesting if you received a 1099-B that shows the proceeds. The IRS will...

Form 8949 and Sch. D diagrams! When I hold restricted stock after it vests and later have capital gains on the sale, will I get any "credit" for the income tax I paid at vesting? This is premium content

The vesting and the sale are separate transactions. First the stock's value at vesting is taxed, unless...

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...

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's the impact of the 2013 tax increases on my restricted stock grants? This is premium content

Increases in tax rates indirectly affect the value of grants. Most importantly...

When my restricted stock vests, will I need to make estimated tax payments? This is premium content

At a minimum, when the restricted stock vests your company will withhold taxes at the required federal withholding rate for...

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...

My company is now granting restricted stock, and the current share price is much lower than I think it will be in a few years. Any tax-planning ideas? This is premium content

For restricted stock, you can make what the tax code calls a Section 83(b) election to be taxed immediately at grant instead of later at vesting, when your stock price, and thus your tax rate, may be much higher. However, before you make your decision, realize that...

How will my broker know which shares to sell? Should I identify them in some way? This is premium content

If you have more than one batch of company stock, you are responsible for providing your broker with enough information to identify which shares to sell. If you do not specify...

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...

When I file an extension to complete my tax return after the IRS deadline, are there any mistakes I should avoid that involve stock grant income? This is premium content

Stock compensation income can raise your income tax and make your tax return complex. The IRS has a form that lets you apply for an automatic six-month extension for the due date of your tax return (until mid-October). Mistakes include not paying taxes owed with...

Can the IRS seize stock options or restricted stock under a tax lien? This is premium content

The IRS can seize your stock options if it applies a federal tax lien to you for unpaid taxes. After seizing your stock options, the IRS can also...

I received a notice (CP-2000) from the IRS stating that, according to last year's tax return, I owe money for the sale of my restricted stock when it vested. I thought I paid all the taxes through withholding at vesting. How do I respond? This is premium content

Because the value of the shares at vesting was added to your W-2, and withholding taxes were based on that value, you thought you did not need to file Schedule D with your Form 1040 to report the sale. It is a common mistake to think this...

In what ways can I pay my taxes if I don't have the money to pay them with my tax return?

If you simply lack the funds to pay your income tax, you may want to apply for a payment agreement on the...

I acquired stock from option exercises and restricted stock vesting a few years ago. When I sell the stock, how do I rediscover the cost basis for my tax return? This is premium content

Let's first review the tax rules and the W-2 reporting. The tax basis for...

Will my income from restricted stock vesting be netted against my short-term capital losses from this year (or those that were carried forward from last year)? This is premium content

The value at vesting is all ordinary income. You have capital gain only for the increase in the stock price after vesting. Only this gain at sale can be...

What is a lapse election, and why do I need to make it before the restricted stock or restricted stock units vest? This is premium content

The "lapse" is the end of the restriction that prevented the shares from vesting and being transferred to you. The lapse election is the method by which you choose withholding methods and what will be done with the...

Should I set up a Rule 10b5-1 trading plan to cover the stock I will sell or surrender to pay withholding taxes when my restricted stock vests? This is premium content

Both Rule 10b5-1 and the broader use of restricted stock and RSUs are new, so practices and procedures are evolving. Companies are considering the widespread use of Rule 10b5-1 plans for this...

When I take an international assignment, will taxes on my stock compensation be equalized? This is premium content

At some companies, international assignments are often accompanied by what is commonly called an equalization package. To give you an incentive to accept the international assignment, the company agrees to...

What is the tax treatment of my restricted stock in an acquisition? This is premium content

This depends on how restricted stock (or restricted stock units) is treated in the acquisition. For example, if the vesting is accelerated, then you will be...

Are my stock grants affected by the rules of deferred compensation under IRC Section 409A? This is premium content

A number of tax law provisions that may affect your stock grants were introduced in the American Jobs Creation Act (AJCA); the final regulations on deferred compensation under IRC Section 409A, which adopt the...

Will my company be able to take a tax deduction for the value of my restricted stock, restricted stock units, performance shares, or stock options if my compensation already exceeds $1 million? This is premium content

This depends on what triggers vesting. Section 162(m) of the tax code limits your company's deduction to $1 million unless a senior officer's compensation over this amount meets the performance-based exception. Stock grants are structured to meet this by...

My new company withheld Social Security tax from my wages even though I maxed out on these taxes this year from my stock option exercise and restricted stock vesting at my prior employer. Can I get a refund or a credit on my tax return? This is premium content

If you have more than one job in a year, each company must withhold Social Security tax without considering what the other company withholds. The result could be...

How soon after my restricted stock vests must the IRS receive my withholding taxes? This is premium content

Companies are still uncertain about the exact timing. With NQSOs, the clock doesn't start ticking until you take action to exercise. However, with restricted stock and RSUs...

May I have my employer withhold more taxes upon the vesting of my restricted stock than the minimum required amount? This is premium content

This can depend on different factors. Whether you can withhold more or not, the mandatory federal withholding rate is...

The value of my restricted stock has fallen since vesting. If I sell my shares at year-end, do I get a credit for the income tax I paid at vesting, or do I net the loss against capital gains? This is premium content

The vesting and the sale are separate transactions and generate different types of income. Unless you made an 83(b) election to be taxed at grant, you were first taxed on the stock's value at vesting, which created ordinary income to you. With restricted stock units (RSUs), taxation occurs...

What happens if I live in state A when my restricted stock is granted, in state B when part of it vests, in state C when the rest of it vests, and in state D when I sell my shares? This is premium content

There is no simple answer to questions involving the taxation of mobile employees. Generally, each state you live in determines what income is taxable and when. For administrative ease, many companies...

If I move to another country to work, will I still have to pay US taxes on option exercises, restricted stock vesting, and stock sales? Can I avoid double taxation? This is premium content

The United States taxes the worldwide income of US citizens regardless of whether the income arises from activities in the US. In addition, the other country may impose taxes too. But the US has tax treaties with certain nations to help taxpayers avoid double taxation...

I'm no longer an employee, so why is there withholding on my restricted stock vesting? This is premium content

Former employees' transactions, regardless of the reason for termination, follow the same withholding and reporting requirements that apply to...

I may leave my company to become a consultant, retire, or take another job. Will taxes still be withheld on my NQSOs, SARs, and/or restricted stock as they were when I was an employee? What if I live in another state when I exercise them? This is premium content

Most companies base withholding on your employment status at the time of grant. If you work elsewhere or are retired at exercise or vesting, then...

I have started receiving Social Security retirement payments. If I exercise stock options or my restricted stock vests, must I still pay Social Security tax on the income? Can this cause my Social Security payments to be taxed too? This is premium content

You pay Social Security and Medicare taxes on all wage and self-employment earnings, regardless of...

Can stock option, restricted stock, or ESPP income alone qualify me to establish an IRA? This is premium content

As long as you meet the other requirements, to be eligible to make contributions under the tax rules you must have "compensation income" that is at least equal to...

I am eligible for vesting acceleration at retirement but have not actually retired, so why has my restricted stock been taxed? Is the treatment different for RSUs? This is premium content

These provisions raise tax complications for both restricted stock and RSU grants, though the issues vary. For tax purposes it does not matter that you must actually retire to vest the shares. With restricted stock, taxation is triggered when the grant is...

The value of my restricted stock at vesting is reported on my W-2 as ordinary income. Can I use my stock-trading losses to offset this income? This is premium content

You have different types of taxable income. The tax law says you can offset losses against only the...

Is the vesting of my restricted stock a "wash sale"? This is premium content

The wash sale rule disallows the loss on a sale of stock if the same type of stock is...

How are shares of company stock that I received from prior option exercises or restricted stock vesting valued for federal estate-tax purposes after my death? Is there a step-up in the basis of the stock? This is premium content

There is a choice. On the date of death, shares of publicly traded companies are generally...

If I die, the vesting of my restricted stock will accelerate. How would this be taxed as part of my estate? This is premium content

Typically, all or a pro rata portion of any restricted stock vests at death. The value of restricted stock that vests and is payable at your death will...

At death, do tax withholding and reporting apply to restricted stock if the vesting is accelerated or allowed to continue? This is premium content

The acceleration and vesting trigger ordinary income. Whether this is W-2 income and taxes are withheld, or whether it is 1099 income, depends on...

What are the federal income tax consequences if my estate or beneficiary sells stock that I received from a prior option exercise or from restricted stock vesting? This is premium content

For federal income tax purposes, your estate or beneficiaries will receive a "step-up" in the tax basis of the shares to the market value of the stock at the time of death...

Does the accelerated vesting of my stock options, restricted stock, and/or performance shares in a change of control or termination have any tax impact on me, such as for ISOs and golden parachute payments? This is premium content

With stock grants of normal size, you face no tax impact beyond the standard tax treatment. ISOs may be converted to NQSOs should any acceleration of vesting cause...

If my restricted stock vests during a blackout period, or if the stock sale on the vest date would trigger Section 16 short-swing profit liability, is the tax treatment delayed until a later date? This is premium content

You are taxed on the full value of the shares at vesting, when the restrictions lapse. It does not matter whether...

My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return? This is premium content

A casualty or theft loss would allow you to deduct the lost amount against your ordinary income, subject to some limits. However, Treasury regulations and court rulings would probably stand in your way. Nevertheless, what you can do is...

What are some year-end strategies for restricted stock and stock options? This is premium content

Decisions in year-end financial and tax planning depend on several factors. In this FAQ, we present several situations and some strategies that many experts suggest. Of course, you should...

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