How to handle capital gains on a Virginia Individual Income Tax Return
In Virginia the maximum tax rate on income is 5.75% which is the same as the capital gains rate. http://www.tax.virginia.gov/income-tax-calculator
As per Indian tax laws; income, expense, gain and loss constitute the basic pillars of every individual’s economic life. There are very few cases under which this new 'income' is non taxable. Based on the circumstances, you might have to pay capital gains tax. In response to your points #1 and #2: In general, yes it is true that capital gains are only subject to half one's marginal rate of income tax.  That doesn't mean 50% of the gain is due as tax... rather, it means that if one's marginal tax rate (tax bracket) on the next $10K would have been, say, 32%, then one is taxed on the gain at 16%.  (The percentages are examples, not factual.) However, because these are employee stock options, the tax treatment is different than for a capital gain!    Details: On the Federal tax return are lines for reporting Security option benefits (Line 101) and Security options deductions (Line 249).  The distinction between a regular capital gain and an employee stock option benefits is important.  In many cases the net effect may be the same as a capital gain, but the income is characterized differently and there are cases where it matters.  Somebody who is about to or has realized employee stock option benefits should seek professional tax advice. In response to your next two points: No, one cannot transfer a capital gain or other investment income into a TFSA immediately after-the-fact in order to receive the tax-free benefits of the TFSA on that income.  Only income and gains earned within a TFSA are free from tax – i.e. The options would have to have been in the TFSA before being exercised.  Once a gain or other investment income has been realized in a non-sheltered account, it is considered taxable.  The horse has already left the barn, so to speak! However, despite the above, there is another strategy available:  One can create an offsetting deduction by contributing some of the realized gain into an RRSP.  The RRSP contribution, assuming room is available, would yield a tax deduction to offset some tax due on the gain.  However, the RRSP only defers income tax; upon withdrawal of funds, ordinary income tax is due (hopefully, at a lower marginal rate in retirement.) There is no minimum amount of time that money or assets have to be inside a TFSA to benefit from the tax-free nature of the account.  However, there are limits on how much money you can move into a TFSA in any given year, and many folks weren't aware of the rules. p.s. Let me add once more that this is a case where I suggest seeking professional tax advice. In the United States investing towards donation is a great idea because you can donate appreciated securities directly rather than donating cash.  Notice how much this can benefit you: So you get to both (a) donate untaxed money and then (b) deduct that unrealized money from your income total on your tax return. With the above in mind, a good strategy for investing towards this type of donation would be to pick securities that are likely to increase in market value but not likely to produce any other sort of income.  So bonds (which produce lots of interest income), or stocks with dividends, or equity mutual funds (which distribute dividends as capital gains) would all be suboptimal for this purpose. Of course, an even better strategy would be to establish a widely diversified investment portfolio without thought to future donations.  Then, once a year (or whenever), evaluate all your investments and find some where the market value has increased.  Then donate some of those shares.  No special advance planning necessary. Note that your tax consequences could be more complicated depending on your exact situation.  Read the section about Capital Gain Property in IRS Pub. 26 for all the details.  There may be special limits on the amount you can deduct.  Also, donations of short term capital gains are treated much less favorably, so make sure you donate only long term capital gain property. "I had been pondering this recently myself too.  This question motivated me to do a little research.  It appears that what happens is that (take a deep breath) the capital gain does push you into the next tax bracket, but the capital gain is always interpreted as the ""last"" income you received, so that if your non-capital-gains income is less than the threshold, it will all be taxed in the lower bracket, and only your capital gain will be taxed in the higher bracket (but it will be taxed at the capital-gains rate of that higher bracket). In short, a capital gain can only push capital gains into higher capital-gains tax brackets; it cannot push ordinary income into higher ordinary-income tax brackets.  In addition, the amount of the capital gain is taxed in a marginal fashion, such that any portion of the gain that will ""fit"" into a lower bracket will be taxed at a lower level, with only the topmost portion of any gain being taxed at the top rate. This site is one claiming this: Will capital gain or dividend income push my other income into a higher tax bracket? No, the tax rates apply first to your “ordinary income” (income from sources other than long-term capital gains or qualifying dividends) so these items that are taxed at special rates won’t push your other income into a higher tax bracket. If my ordinary income puts me in the 15% tax bracket, can I receive an unlimited amount of long-term capital gain at the 0% rate? No, the 0% rate applies only to the amount of long-term capital gain and dividend income needed to “fill up” the 15% tax bracket. For example, if your ordinary income is $4,000 below the figure that would put you in the 25% bracket and you have a $10,000 long-term capital gain, you’ll pay 0% on $4,000 of your capital gain and 15% on the rest. There are several Bogleheads forum threads (here, here, here and here) that also touch on the same issue. The last of those links to the IRS capital gains worksheet.  I traced through the logic and I believe it confirms this.  Here's how it works: (In conclusion, we now know Mitt Romney's secret.)" "Taxes are triggered when you sell the individual stock.      The IRS doesn't care which of your accounts the money is in.  They view all your bank and brokerage accounts as if they are one big account mashed together.   That kind of lumping is standard accounting practice for businesses. P/L, balance sheets, cash flow statements etc. will clump cash accounts as ""cash"".  Taxes are also triggered when they pay you a dividend.  That's why ETFs are preferable to mutual funds; ETFs automatically fold the dividends back into the ETF's value, so it doesn't cause a taxable event.  Less paperwork.  None of the above applies to retirement accounts.  They are special.  You don't report activity inside retirement accounts, because it would be very hard for regular folk to do that reporting, so that would discourage them from taking IRAs.   Taxes are paid at withdrawal time (or in Roth's, never.)" Such activity is normally referred to as bartering income. From the IRS site - You must include in gross income in the year of receipt the fair market value of goods or services received from bartering. Generally, you report this income on Form 1040, Schedule C (PDF), Profit or Loss from Business (Sole Proprietorship), or Form 1040, Schedule C-EZ (PDF), Net Profit from Business (Sole Proprietorship). If you failed to report this income, correct your return by filing a Form 1040X (PDF), Amended U.S. Individual Income Tax Return. Refer to Topic 308 and Amended Returns for information on filing an amended return. "You pay tax on the entire amount, not just the capital gains.   When cashing out such a plan you would pay the top marginal tax rate on the full amount plus another 10% in penalties.  It is very likely that the additional income, of the balance withdrawal, will increase your top marginal rate.   It is impossible to come up with a precise answer as we don't know the following: However, you can take a concept away from this that is important:  You will be taxed and penalized on the entire 401K balance, not just the capital gain.   In the ""best case"" scenario, that is you had little or no income in a given year.  Under current tax law you would owe about 31% of your 401K balance in taxes.  As this is such an inefficient use of money most authors recommend against it except in the case of extreme circumstances." I am not a tax professional, only an investment professional, so please take the following with a grain of salt and simply as informational guidance, not a personal recommendation or solicitation to buy/sell any security or as personal tax or investment advice. As Ross mentioned, you need to consult a tax advisor for a final answer concerning your friend's personal circumstances. In my experience advising hundreds of clients (and working directly with their tax advisors) the cost basis is used to calculate tax gain or loss on ordinary investments in the US. It appears to me that the Edward Jones description is correct. This has also been the case for me personally in the US with a variety of securities--stocks, options, futures, bonds, mutual funds, and exchange traded funds.  From the IRS: https://www.irs.gov/uac/about-form-1099b Form 1099-B, Proceeds From Broker and Barter Exchange Transactions A broker or barter exchange must file this form for each person: Edward Jones should be able to produce a 1099b documenting the gains/losses of any investments. If the 1099b document is confusing, they might have a gain/loss report that more clearly delineates proceeds, capital returns, dividends, and other items related to the purchase and sale of securities.