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I have made substantial gains in the stock market this year on stocks that I have held long term (> 1 year).

I understand that when I sell this stock, I will pay 15% capital gains tax.

I have heard that the capital gains tax is going up to 20%.

Three questions:

  1. Is this true?

  2. When is the last day I can sell my stock to lock-in the 15% rate?

  3. When is the earliest I can rebuy the same stock without getting into trouble with the IRS? Ideally I would sell it immediately to lock-in gains taxable at 15% and then re-buy, so I assume the IRS has considered this loophole.

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To the new visitor - This question dealt with tax changes which were scheduled to happen at the beginning of 2011. Those changes never happened. However, as of November 2012, very similar changes are scheduled to happen at the beginning of 2012. To Congress: Hey, 2010 called. They want their fiscal-policy uncertainty back. –  fennec Nov 28 '12 at 4:26
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To the new visitor - In the third sentence of @fennec's comment, read "... beginning of 2013" instead of "... beginning of 2012." –  Dilip Sarwate Nov 28 '12 at 11:32
    
dangit I keep typoing it. stupid years. who needs 'em. –  fennec Dec 4 '12 at 1:48

3 Answers 3

up vote 6 down vote accepted

The top long-term capital gains tax rate will rise to 20% effective 1 Jan, 2011, unless Congress decides to do something about it before then. (Will they? Who knows!! There's been talk about it, but, well, it's Congress. They don't even know what they're going to do.)

Anyway. The rules about when you can sell stock are mostly concerned with when you can realize a capital loss: if you sell a stock at a loss and then re-buy it for tax purposes within 30 days, it's a wash sale and not eligible for a deduction. However, I don't believe this applies to any stocks once you realize a gain - once you've realized the gain and paid your tax for it, it's all yours, locked in at whatever rate. Your replacement stock will be subject to short-term capital gains for the next year afterwards, and you might need to be careful with identifying the holding period on different lots of your stock, but I don't believe there will be any particular trouble.

Please do not rely entirely on my advice and consult also with your tax preparer or lawyer. :) And the IRS documentation:

Special Addendum for Nov/Dec 2012! Spoiler alert! Congress did indeed act: they extended the rates, but only temporarily, so now we're looking at tax hikes starting in 2013 instead, only the new top rate++ will be something like 23.8% on account of an extra 3.8% medicare tax on passive earnings (brought to you via Obamacare legislation). But the year and the rates' specifics aside, same thing still applies. And the Republican house and Democratic senate/President are still duking it out. Have fun.

++ 3.8% surtax applies to the lesser of (a) net investment income (b) income over $200,000 ($250k if married). 20% tax rate applies to people in the 15% income tax bracket for ordinary income or higher. Additional tax discounts for property held over 5 years may be available. Consult tax law and your favorite tax professional and prepare to be confused.

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Also, if you think that tax jump is crazy and gives you weird incentives, you should see the estate tax... it's going from 0 to 55%. –  fennec Nov 29 '10 at 21:09
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2010? Did you mean 2011? –  MrChrister Nov 29 '10 at 22:45
    
So really, everyone should sell their stock to lock-in gains and then immediately rebuy? Is there a way to profit off the need for large mutual funds to do this by Jan 1? An derivative that increases in value when the volume of the underlying security goes up? –  John Shedletsky Nov 30 '10 at 19:18
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Actually it's going to be 2013. ;-) –  Jon S Aug 22 '12 at 16:37
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The sell/buy to pull the gain into this year can make sense for some. The flip side is that inherited stocks get a step up in basis, and avoid the cap gain completely. So a hold for life stock should just be held. –  JoeTaxpayer Nov 28 '12 at 1:14

For the record, now that 2011 is here we know that the capital gains tax rate didn't change. Congress extended it for two more years.

This shows the uncertainty in trying to maximize earnings based on future changes to the tax code.

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Consider doing things that will allow for tax deductions, such as short selling. The IRS has regulations on this as well.

And consider that Futures are taxed more favorably than other kinds of investments. (60% taxed as long term, 40% taxed as short term)

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Since I got downvoted for correct information, I have included links to official IRS taxation information: irs.gov/publications/p550/ch04.html and search "60/40 rule" without quotes and also read about the wash sale rules in regards to short selling –  RD. Jul 19 '11 at 20:16
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Since this question is coming up again now that it's 2013-cliff-season, I'll explain: you were downvoted because the original poster is concerned about primarily stock-related investments, and short-sold stocks and futures have significantly different behaviors and characteristics governing their risk and returns. They do not represent an effective substitute for the bulk of those investments. Your advice to consider them is only marginally more useful than if you had told them of some hypothetical way to avoid taxes by investing in rare artwork and tulip bulbs. –  fennec Nov 28 '12 at 4:01

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