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Tax Center: Tax Changes 2003–2012


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NEW! A podcast on this year's new tax forms and reporting rules for stock sales!

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

Bruce Brumberg
NEW! 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! New Tax Return Forms & Reporting Rules For Stock Sales

Bruce Brumberg
If there's a way to make learning about tax forms fun, we'll try it. Watch and hear this animated presentation on the expanded IRS Form 1099-B, the new IRS Form 8949, and the revised Schedule D. Learn now to prevent costly tax return mistakes later!

How The Bush Tax Cuts Still Affect Your Stock Option Planning

Tom Davison
Even under President Barack Obama, the Bush administration's 2003 tax cuts and later extensions (now through 2012) continue to affect tax strategies for NQSOs, ISOs, and restricted stock.

How Tax Rate Changes Impact Your Stock Grant Strategies (Part 1): Nonqualified Stock Options This is premium content

Stanley Trotta with Robert Gordon
With tax increases possible in the future, now may be a good time to re-evaluate your current financial-planning strategy. Should you take action with stock options now or wait until new rates apply? Part 1 looks at nonqualified stock options.

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. Should you take action with stock compensation now or wait until new rates apply? Part 2 looks at restricted stock and restricted stock units.

How Tax Rate Changes Impact Your Stock Grant Strategies (Part 3): Incentive Stock Options 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. Should you take action with stock options now or wait until new rates apply? Part 3 looks at incentive stock options.

Refundable AMT Credit: Different Rules For Old Unused Credit

Kaye A. Thomas
Special rules for old unused AMT credits, first available in 2007, were drastically revised for the tax years 2008 through 2012. This is the first of two articles on the refundable AMT credit, which provides a way for many people to use more AMT credits than they could under the regular rules.

Refundable AMT Credit: The Calculation

Kaye A. Thomas
Special rules for old unused AMT credits, first available in 2007, were drastically revised for the tax years 2008 through 2012. This is the second of two articles on the refundable AMT credit, which provides a way for many people to use more AMT credits than they could under the regular rules.

How Dividends Impact Your Strategy For Stock Options And Restricted Stock (Part 1) This is premium content

Tom Davison
With the lower tax rate on dividends, let's look at the effects of dividends on your planning for stock options and restricted stock.

How Dividends Impact Your Strategy For Stock Options And Restricted Stock (Part 2) This is premium content

Tom Davison
The lower tax rate on dividends may change your stock option and restricted stock planning. Part 1 explained basic dividend rules. This article looks at dividend strategy.

President Signs Two-Year Extension Of Bush-Era Tax Cuts, Payroll Tax Relief, Estate Tax Compromise

CCH
This CCH Tax Briefing concisely summarizes the major provisions in the 2010 Tax Relief Act, including those which affect stock compensation.

IRS Publication 550: Investment Income And Expenses

Internal Revenue Service
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).

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NEW! What are the big changes with reporting stock sales this year on my tax return? Why have these changes occurred?

For people who sold shares in 2011, major changes in tax reporting and filing are taking effect this tax season...

NEW! How is IRS Form 1099-B changing for sales of stock acquired from my stock options, restricted stock, or ESPP? This is premium content

More information is now reported on this form than in past years. This may prove to be more helpful, but it also may be more confusing. Issued to you by your brokerage firm, IRS Form 1099-B is an important document that you must have to complete your tax return. Recent legislation has changed the form in significant ways that you must understand...

NEW! 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...

UPDATED! Is the spread at exercise of a nonqualified stock option subject to Social Security taxes? This is premium content

Yes. The spread at exercise of an NQSO is "wages" for purposes of...

UPDATED! 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

When 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...

UPDATED! How and when are taxes withheld from my restricted stock? This is premium content

Restricted stock withholding is similar to withholding for most other forms of supplemental compensation. You can have different choices for paying taxes, or your company may automatically...

UPDATED! What is "capital gain"? Have recent tax laws changed the capital gains tax rates?

"Capital gain" is income that arises from the sale of a capital asset. Gain from the sale of shares acquired from option exercise or restricted stock vesting is...

NEW! 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...

When does my holding period for the special tax rate on dividends begin? At exercise or vesting? This is premium content

The holding period to determine whether a dividend is "qualified" and taxed at the lower 15% rate starts on the date after the option is exercised and the stock is held...

If my brokerage firm lends my dividend-paying company shares while I have a margin loan, will the dividends qualify for the special 15% tax rate? This is premium content

If you take out a margin loan from your brokerage firm, it can lend your shares to short sellers. If that stock pays a dividend while your shares are on loan, you will...

My company pays a good dividend. Assuming I hold the stock long enough, my dividends and capital gains are now taxed at 15%. Should I exercise and hold my NQSOs instead of just waiting to exercise near the end of the option term? This is premium content

The traditional strategy with NQSOs recommends waiting till...

If I borrow money to exercise my options, can I deduct the interest payments against dividend income from my company stock? This is premium content

Maybe not. You are probably thinking that you can borrow money, such as with a margin loan, deduct this as an investment interest deduction, and net it against investment income...

UPDATED! Are there any stock-option strategies for using my capital-loss carry-forwards? This is premium content

Tax considerations alone should not drive the choice of what stock you sell. For example, if you are holding appreciated company stock from a nonqualified stock option (NQSO) exercise, you will be taxed on any capital gains when you sell it. The capital-loss carry-forward from last year's unused losses can offset these gains, making it less "taxing" to diversify your holdings...

Both dividends and long-term capital gains are now taxed at the same rate. Can I net my dividends from my company stock against capital loss from the sale of company stock or another security? This is premium content

No. Under the 2003 tax cut, qualified dividends are taxed at the same rates as long-term capital gains...

Will the amount of tax withheld at NQSO exercise cover the amount of tax that I am required to pay when I file my return? This is premium content

Not necessarily. Employers usually withhold federal income taxes at the rate used for supplemental wages...

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...

If I exercise ISOs and hold the stock (triggering AMT for the spread) or sell the stock in a disqualifying disposition, will I need to make estimated tax payments? This is premium content

You need to pay enough tax during the year through withholding or estimated tax payments to avoid penalties and interest. The tax that has to be paid includes any AMT attributable to the exercise of ISOs or any ordinary income from a disqualifying disposition. In these ISO situations, your employer does not...

What is the latest news about AMT legislation in Congress?

To keep middle-income people from being unfairly hit by the alternative minimum tax, Congress has enacted temporary relief during each of the past few years. These include legislative "patches" to extend and increase the income exemption amounts that apply to the AMT...

UPDATED! What impact does the 2010 Tax Relief Act have on stock compensation and financial planning?

The 2010 Tax Relief Act extended the 2010 tax rates through 2012. This FAQ presents eight related planning points for equity compensation...

Now that the 2010 Tax Relief Act has been passed, why do the provisions in the 2003 tax law still affect my strategy for stock options and restricted stock?

The 2003 tax law has no provisions that deal directly with employee stock options or stock purchase plans. If your income goes up...

Can stock grant income affect my eligibility for the Making Work Pay Credit?

The Making Work Pay Credit was created by the American Recovery & Reinvestment Act of 2009. It was replaced in 2011 by a 2% reduction in the Social Security tax rate. This rate cut was part of the 2010 Tax Relief Act...

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   Tax Center   
Reporting Company Stock Sales   
Tax Changes 2003–2012   
NQSO Basics   
NQSO Withholding   
NQSOs: W-2s & Tax Returns   
ISO Basics   
ISO Withholding   
ISOs: W-2s & Tax Returns   
Restricted Stock Basics   
Restricted Stock Withholding   
Restricted Stock: W-2s & Tax Returns   
Section 83(b)   
ESPP Basics   
ESPP Withholding   
ESPPs: W-2s & Tax Returns   
SARs: W-2s & Tax Returns   
Global Tax Guide   

Annotated diagram of Schedule DTax errors can be costly! Don't draw unwanted attention from the IRS. Our Tax Center explains and illustrates the tax rules for sales of company stock, W-2s, withholding, estimated taxes, AMT, and more.