What US taxes are due for US stock bought via ESPP when I was in USA and sold after I returned to India?
From an Indian Tax point of view, you can bring back all the assets acquired during the period you were NRI back to India tax free. Subject to a 7 years period. i.e. all the assets / funds / etc should be brought back to India within 7 years. It would still be treated as There are certain conditions / paperwork. Please consult a CA.
Reading IRS Regulations section 15a.453-1(c) more closely, I see that this was a contingent payment sale with a stated maximum selling price. Therefore, at the time of filing prior years, there was no way of knowing the final contingent payment would not be reached and thus the prior years were filed correctly and should not be amended. Those regulations go on to give an example of a sale with a stated maximum selling price where the maximum was not reached due to contingency and states that in such cases: When the maximum [payment] amount is subsequently reduced, the gross profit ratio will be recomputed with respect to payments received in or after the taxable year in which an event requiring reduction occurs. However, in this case, that would result in a negative gross profit ratio on line 19 of form 6252 which Turbo Tax reports should be a non-negative number.  Looking further in the regulations, I found an example which relates to bankruptcy and a resulting loss in a subsequent year: For 1992 A will report a loss of $5 million attributable to the sale, taken at the time determined to be appropriate under the rules generally applicable to worthless debts. Therefore, I used a gross profit ratio of zero on line 19 and entered a separate stock sale not reported on a 1099-B as a worthless stock on Form 8949 as a capital loss based upon the remaining basis in the stock sold in an installment sale.  I also included an explanatory statement with my return to the IRS stating: In 2008, I entered into an installment sale of stock. The sale was a contingent payment sale with a stated maximum selling price. The sales price did not reach the agreed upon maximum sales price due to some contingencies not being met. According to the IRS   Regulations section 15a.453-1(c) my basis in the stock remains at $500 in 2012 after the final payment. Rather than using a negative gross profit ratio on line 19 of form 6252, I'm using a zero ratio and treating the remaining basis as a schedule-D loss similar to worthless stock since the sale is now complete and my remaining basis is no longer recoverable. I don't think you are reading the stock chart right.  ORCL has a beta of 1.12 which means it has more volatility than the market as a whole.  See image below for a fairly wild stock chart for a year.   I would not truly consider ESPP participation investing, unless you intend to buy and hold the stock.  If you intend to sell the stock soon after you are able, it is more speculation.  ESPP's are okay based upon the terms.  If the stock was a constant price, and you could sell right away, then an ESPP plan would be easy money.  Often, employees are often given a 15% discount to purchase the stock.  If you can sell it before any price drop, then you are guaranteed to make 15% on the money invested minus any commissions.   Some employers make ESPP participants hold the stock for a year.  This makes such a plan less of a value.  The reasons are the stock can drop in price during that time, you could need the money, or (in the best case) your money is tied up longer making the ROI less. The reasons people invest in stock are varied and is far to much to discuss in a single post.  Some of your colleagues are using the ESPP solely to earn the discount in their money. I have an ESPP with E*Trade; you can transfer stock like that via a physical (paper) asset-transfer form. Look for one of those, and if you can't find it, call your brokerage (or email / whatever). You own the shares, so you can generally do what you want with them. Just be very careful about recording all the purchase and transfer information so that you can deal properly with the taxes. "Sounds like your grandmother's estate had taxable income and the estate did not pay the estate ""INCOME"" tax.  Rather the estate shifted the burden to pay that tax on the beneficiaries which is why you received a K1.  If that K1 reports income received by you, then YES you would have to amend your tax return.  I am in exactly that same situation now.  After the October 15 deadline to file 2012 tax returns, I received a K1 for income received from my dad's estate.  I now have to file a late amended 2012 income tax return and pay income tax on what I inherited. My dad had a small estate, but the money that made up that small estate all came from an IRA he had.  He designated the estate as his beneficiary.  So when the stocks in the IRA were sold, that all became taxable income to the beneficiaries of the estate. Anything involving taxes is confusing at best.  But do not confuse estate income tax, with estate tax -- they are two different taxes. Hope this helps." It was not 100% clear if you have held all of these stocks for over a year.  Therefore, depending on your income tax bracket, it might make sense to hold on to the stock until you have held the individual stock for a year to only be taxed at long-term capital gains rates.  Also, you need to take into account the Net Investment Income Tax(NIIT), if your current modified adjusted income is above the current threshold.  Beyond these, I would think that you would want to apply the same methodology that caused you to buy these in the first place, as it seems to be working well for you. 2 & 3. No.  You trigger a taxable event and therefore have to pay capital gains tax on any gains.  If you have a loss in the stock and repurchase the stock within 30 days, you don't get to recognize the loss and have to add the loss to your basis in the stock (Wash Sales Rules). How you are taxed will depend on what kind of stock awards they are. The value will be determined by the company that issues it, and appropriate tax forms will be sent to you to include with your taxes. The way the value is determined is an accounting question that is off-topic here, but the value will be stated on your stock award paperwork. If you are awarded the stock directly then that value will be taxed as ordinary income. If you are awarded options, then you can purchase the stock to start the clock on long-term capital gains, but you will not incur any tax liability through the initial purchase.  If the company is sold privately and you have held the stock for over 1 year, then yes, it will be taxed as a long-term capital gain. If you receive/exercise the stock less than 1 year before such an acquisition, then it will be considered a short-term capital gain and will be taxed as ordinary income. Will I able to put the Rs amount back in the NRE account the same amount which I have paid against that house? If you have purchased the property by debiting an NRE account [you should have the paper trail], the same amount of funds can be transferred back to NRE Account. For example the house was for 50 lacs, and you paid Rs 30 lacs from NRE account, when you sell the house, you can transfer back only 30 lacs into the NRE account. Will I need to pay TAX on NRE account money before transferring out of India? You need not pay tax on the funds in NRE account. However if you have made gains by buying and selling a house [irrespective of the source of funds], you have to pay capital gains tax. Sale of a stock creates a capital gain. It can be offset with losses, up to $3000 more than the gains. It can be deferred when held within a retirement account.  When you gift appreciated stock, the basis follows. So when I gifted my daughter's trust shares, there was still tax due upon sale. The kiddy tax helped reduce but not eliminate it. And there was no quotes around ownership. The money is gone, her account is for college.  No 1031 exchange exists for stock.