Selling stocks - capital gains
In the US you specify explicitly what stocks you're selling. Brokers now are required to keep track of cost basis and report it to the IRS on the 1099-B, so you have to tell the broker which position it is that you're closing. Usually, the default is FIFO (i.e.: when you sell, you're assumed to be closing the oldest position), but you can change it if you want. In the US you cannot average costs basis of stocks (you can for mutual funds), so you either do FIFO, LIFO (last position closed first), or specify the specific positions when you submit the sale order.
"The wash sale rule only applies when the sale in question is at a loss.  So the rule does not apply at all to your cases 3, 4, 7, 8, 11, 12, 15, and 16, which all start with a gain.  You get a capital gain at the first sale and then a separately computed gain / loss at the second sale, depending on the case, BUT any gain or loss in the IRA is not a taxable event due to the usual tax-advantaged rules for the IRA. The wash sale does not apply to ""first"" sales in your IRA because there is no taxable gain or loss in that case.  That means that you wouldn't be seeking a deduction anyway, and there is nothing to get rolled into the repurchase. This means that the rule does not apply to 1-8.  For 5-8, where the second sale is in your brokerage account, you have a ""usual"" capital gain / loss as if the sale in the IRA didn't happen. (For 1-4, again, the second sale is in the IRA, so that sale is not taxable.) What's left are 9-10 (Brokerage -> IRA) and 13-14 (Brokerage -> Brokerage).   The easier two are 13-14.  In this case, you cannot take a capital loss deduction for the first sale at a loss.  The loss gets added to the basis of the repurchase instead.  When you ultimately close the position with the second sale, then you compute your gain or loss based on the modified basis.  Note that this means you need to be careful about what you mean by ""gain"" or ""loss"" at the second sale, because you need to be careful about when you account for the basis adjustment due to the wash sale. Example 1: All buys and sells are in your brokerage account.  You buy initially at $10 and sell at $8, creating a $2 loss.  But you buy again within the wash sale window at $9 and sell that at $12.  You get no deduction after the first sale because it's wash.  You have a $1 capital gain at the second sale because your basis is $11 = $9 + $2 due to the $2 basis adjustment from wash sale. Example 2: Same as Example 1, except that final sale is at $8 instead of at $12.  In this case you appear to have taken a $2 loss on the first buy-sell and another $1 loss on the second buy-sell.  For taxes however, you cannot claim the loss at the first sale due to the wash.  At the second sale, your basis is still $11 (as in Example 1), so your overall capital loss is the $3 dollars that you might expect, computed as the $8 final sale price minus the $11 (wash-adjusted) basis. Now for 9-10 (Brokerage->IRA), things are a little more complicated.  In the IRA, you don't worry about the basis of individual stocks that you hold because of the way that tax advantages of those accounts work.  You do need to worry about the basis of the IRA account as a whole, however, in some cases.  The most common case would be if you have non-deductable contributions to your traditional IRA.  When you eventually withdraw, you don't pay tax on any distributions that are attributable to those nondeductible contributions (because you already paid tax on that part).  There are other cases where basis of your account matters, but that's a whole question in itself - It's enough for now to understand 1. Basis in your IRA as a whole is a well-defined concept with tax implications, and 2. Basis in individual holdings within your account don't matter. So with the brokerage-IRA wash sale, there are two questions:  1. Can you take the capital loss on the brokerage side?  2. If no because of the wash sale, does this increase the basis of your IRA account (as a whole)?  The answer to both is ""no,"" although the reason is not obvious. The IRS actually put out a Special Bulletin to answer the question specifically because it was unclear in the law. Bottom line for 9-10 is that you apparently are losing your tax deduction completely in that case. In addition, if you were counting on an increase in the basis of your IRA to avoid early distribution penalties, you don't get that either, which will result in yet more tax if you actually take the early distribution. In addition to the Special Bulletin noted above, Publication 550, which talks about wash sale rules for individuals, may also help some." You don't. When you sell them - your cost basis would be the price of the stock at which you sold the stocks to cover the taxes, and the difference is your regular capital gain. Consult a professional CA. For shares sold outside the Indian Stock Exchanges, these will be treated as normal Long Term Capital Gains if held more than one year. The rate would be 10% without Indexation and 20% with Indexation. If the stocks are held for less than 1 years, it will be short term gains and taxed according you to tax bracket. Yes, you would have to report the gain. It is not relevant that you traded the stock previously, you still made a profit on the trade-at-hand. Imagine if for some reason this type of trade were exempt. Investors could follow the short term swings of volatile stocks completely tax-free. You need to report the income from any work as income, regardless of if you invest it, spend it, or put it in your mattress (ignoring tax advantaged accounts like 401ks).  You then also need to report any realized gains or losses from non-tax advantaged accounts, as well as any dividends received.  Gains and losses are realized when you actually sell, and is the difference between the price you bought for, and the price you sold for.  Gains are taxed at the capital gains rate, either short-term or long-term depending on how long you owned the stock.   The tax system is complex, and these are just the general rules.  There are lots of complications and special situations, some things are different depending on how much you make, etc.  The IRS has all of the forms and rules online.  You might also consider having a professional do you taxes the first time, just to ensure that they are done correctly.  You can then use that as an example in future years. Here's an article on it that might help: http://thefinancebuff.com/restricted-stock-units-rsu-sales-and.html One of the tricky things is that you probably have the value of the vested shares and withheld taxes already on your W-2. This confuses everyone including the IRS (they sent me one of those audits-by-mail one year, where the issue was they wanted to double-count stock compensation that was on both 1099-B and W-2; a quick letter explaining this and they were happy). The general idea is that when you first irrevocably own the stock (it vests) then that's income, because you're receiving something of value. So this goes on a W-2 and is taxed as income, not capital gains. Conceptually you've just spent however many dollars in income to buy stock, so that's your basis on the stock. For tax paid, if your employer withheld taxes, it should be included in your W-2. In that case you would not separately list it elsewhere. When you sell a stock that you own, you realize gains, or losses. Short-term gains, realized within a year of buying and selling an asset, are taxed at your maximum (or marginal) tax rate. Long term-gains, realized after a year, are taxed at a lower, preferential rate. The first thing to consider is losses. Losses can be cancelled against gains, reducing your tax liability. Losses can also be carried over to the next tax year and be redeemed against those gains. When you own a bunch of the same type of stock, bought at different times and prices, you can choose which shares to sell. This allows you to decide whether you realize short- or long-term gains (or losses). This is known as lot matching (or order matching). You want to sell the shares that lost value before selling the ones that gained value. Booking losses reduces your taxes; booking gains increases them. If faced with a choice between booking short term and long term losses, I'd go with the former. Since net short-term gains are taxed at a higher rate, I'd want to minimize the short-term tax liability before moving on to long-term tax liability. If my remaining shares had gains, I'd sell the ones purchased earliest since long-term gains are taxed at a lower rate, and delaying the booking of gains converts short-term gains into long-term ones. If there's a formula for this, I'd say it's  (profit - loss) x (tax bracket) = tax paid "You uncle is liable to pay ""Capital-Gains"" tax. Essentially the sale price less of cost would be treated as gains. The gains are taxed at 10% without indexation and 20% with Indexation.  The capital gains tax can be avoided if your uncle invests the gains into specified ""Infrastructure bonds"" or buys another property within a period of 3 years. The funds need to be kept in a separate ""Capital Gains"" account and not a regular savings account till you buy another property within 3 years." "In the US, and in most other countries, dividends are considered income when paid, and capital gains/losses are considered income/loss when realized. This is called, in accounting, ""recognition"". We recognize income when cash reaches our pocket, for tax purposes. So for dividends - it is when they're paid, and for gains - when you actually sell. Assuming the price of that fund never changes, you have this math do to when you sell: Of course, the capital loss/gain may change by the time you actually sell and realize it, but assuming the only price change is due to the dividends payout - it's a wash." It would be better for you to sell yourself and pay capital gains tax than to transfer to your parents and pay the gift tax. Also, sham transfer (you transfer to your mother only so that she could sell and transfer back to you without you paying taxes) will be probably categorized as tax evasion, which is a criminal offense that could lead to your deportation. What the US should or should not claim you can take to your congressman, but the fact is that the US does claim tax on capital gains even if you bought the asset before becoming US tax resident, and that's the current law. does it still count as a capital gain or loss? Yes. Is it essentially treated like you sold the stock at the price of the buy-out?  Yes. Do you still get a 1099-B from your broker? Yes. You wouldn't fill out a 1099, your employer would or possibly whoever manages the stock account.   The 1099-B imported from E-Trade says I had a transaction with sell price ~$4,500.   Yes.  You sold ~$4500 of stock to pay income taxes.  Both the cost basis and the sale price would probably be ~$4500, so no capital gain.  This is because you received and sold the stock at the same time.  If they waited a little, you could have had a small gain or loss.   The remainder of the stock has a cost basis of ~$5500.   There are at least two transactions here.   In the future you may sell the remaining stock.  It has a cost basis of ~$5500.  Sale price of course unknown until then.  You may break that into different pieces.  So you might sell $500 of cost basis for $1000 with a ~$500 capital gain.  Then later sell the remainder for $15,000 for a capital gain of ~$10,000. "You're right.  I did include ""is it reasonable"" in the title.  Therefore that brings in the acceptability of those taxes.  However I am making the case that I would like capital gains to be taxed most similarly to regular income (or at least in a parallel bracket), which is independent of the amount needed to be brought in.  I think parallel brackets would be the most productive since it would encourage people to both produce and invest, because you would get the lowest taxes by maximizing both." For ESPP, the discount that you get is taxed as ordinary income. Capital gains is taxed at the appropriate rate, which is different based on how long you hold it. So, yes, if the stock is going up, The sentence you quoted does not apply in the case where you sell the stock at a loss. In that case, you recognize zero ordinary income, and a capital loss (opposite of a gain) for the loss. Reference: http://efs.fidelity.com/support/sps/article/article2.html