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Tax Center: Tax Cuts 2003–2008


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How The Bush Tax Cuts Still Affect Your Stock Option Planning

Tom Davison
UPDATED! Even under the new president, the Bush administration's 2003 tax cuts and later extensions will continue to affect tax strategies for NQSOs, ISOs, and restricted stock. Unless these tax laws change sooner, many of them will persist through 2010.

Refundable AMT Credit (Part 1): Different Rules For Old Unused Credit

Kaye A. Thomas
UPDATED! Beginning with tax returns for the tax year 2007, certain taxpayers are able to claim old unused AMT credit even if it means getting a refund that exceeds the current year's tax. This pair of articles provides complete coverage of the refundable AMT credit, which provides a way for many people to use more AMT credit than under the regular rules.

Refundable AMT Credit (Part 2): The Calculation

Kaye A. Thomas
UPDATED! The refundable AMT credit will be a boon to many taxpayers, especially those who encountered disaster with incentive stock options during the tech stock collapse that began in 2000. This pair of articles provides complete coverage of the refundable credit.

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.

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).

Advisors To Clients: Prepare For Likely Tax Increases

Lisa Shidler
Investment News
Considering the likelihood of tax increases after 2008, some advisors (and their clients) want to sell at least some shares now, while the top capital gains rate is still only 15%. Other advisors suggest waiting, as stocks are low and gains from an eventual market upswing may outweigh any potential tax savings.

Tax Changes Coming, But When?

Andrea Coombes
MarketWatch
The pressures of the economic downturn may delay the tax reforms that President Barack Obama wants, but eventually at least some of them will probably occur.

D'oh! The Qualified Dividend Glitch

Kaye Thomas
Fairmark Press Tax Guide For Investors
You have to hold the shares at least 61 days if you want to claim the lower qualified dividend tax rate. The holding period calculation is tricky.

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UPDATED! If I did not qualify for a tax rebate under the Economic Stimulus Act in 2008, can I still qualify in 2009?

Possibly. The Economic Stimulus Act of 2008, signed into law in February 2008, created a tax rebate for many people whose income, as reported on tax returns for 2007, qualified them to receive the rebate. However, in some situations this tax break can also be used to reduce taxes on your return for the 2008 tax year...

UPDATED! What is the alternative minimum tax (AMT)? What is the latest news about AMT reform in Congress?

Running parallel to the regular tax system, the alternative minimum tax (AMT) was established in 1969 to require the super-wealthy to pay taxes when credits and other deductions could otherwise reduce or eliminate their tax altogether. However, for several reasons, over the years the AMT has started to hit a growing number of taxpayers who aren't wealthy, and also people who exercise incentive stock options (ISOs). Congress has enacted temporary AMT relief to protect middle-income taxpayers from the AMT, and in 2008 significantly changed the rules governing the use of AMT credits...

UPDATED! Has recent legislation changed the taxation of incentive stock options? This is premium content

While the 2003 tax law did not change the taxation of ISOs, there were a few changes that impact the tax when you sell the stock. Tax law changes in 2006, 2007, and 2008 raised the AMT income exemption amounts and provided an alternative way to use AMT credits...

UPDATED! In general, how does the alternative minimum tax (AMT) calculation work?

The AMT system is complicated. Broadly, it starts by taking your adjusted gross income, subtracts your itemized deductions, makes certain negative and positive adjustments, and includes certain tax items called tax "preferences." The resulting amount...

What provisions in the 2003 tax law still affect my stock option strategy?

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

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

"Capital gain" is income that arises from the sale of a capital asset. Gain from the sale of securities held for investment...

Schedule D diagram! How are capital gains taxed when I sell my NQSO stock? This is premium content

If you hold stock acquired from the exercise of an NQSO for more than one year, the appreciation is...

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 an attractive 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...

What is the capital gains tax rate at sale if the stock options were granted or exercised before the lower capital gains rates went into effect in 2003? This is premium content

For stock held at least one year and sold on or after May 6, 2003, the top rate of tax...

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...

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Featured FAQs
UPDATED! If I did not qualify for a tax rebate under the Economic Stimulus Act in 2008, can I still qualify in 2009?
Possibly. The Economic Stimulus Act of 2008, signed into law in February 2008, created a tax rebate for many people whose income, as reported on tax returns for 2007, qualified them to receive the rebate. However, in some situations this tax break can also be used to reduce taxes on your return for the 2008 tax year...
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...