Do I need to report a capital gain/loss for stock given as a bonus and already taxed?
If you received shares as part of a bonus you needed to pay income tax on the dollar valuse of those shares at the time you received them. This income tax is based on the dollar value of the bonus and has nothing to do with the shares. If you have since sold these shares you will need to report any capital gain or loss you made from their dollar value when you received them. If you made a gain you would need to pay capital gains tax on the profits (if you held them for more than a year you would get a discount on the capital gains tax you have to pay). If you made a loss you can use that capital loss to reduce any other capital gains in that income year, reduce any other income up to $3000 per year, or carry any additional capital loss forward to future income years to reduce any gains or income (up to $3000 per year) you do have in the future.
Stock awards by employers are treated and taxed as salary. I.e.: you pay ordinary rate income tax, FICA taxes, State taxes etc. The fact that you got your salary in shares and not cash is irrelevant for tax purposes. Once you got the shares and paid your taxes on them, the treatment is the same as if you got the salary and immediately bought the shares. Holding period for capital gains tax purposes starts at the time you paid your taxes on the award, which is the time at which you get full ownership (i.e.: vesting time, for the restricted stocks). When you sell these stocks - you treat the sale as any other stock sale: you check the holding period for capital gains tax rates, and you do not pay (or get refund) any FICA taxes on the sales transaction. So bottom line: You got $10K salary and you bought $10K worth of company stock, and you sold it at $8K half a year later. You have $10K wages income and $2K short term capital loss. There is no limit on how much money you can bring into the USA, in Cash or through electronic transfer. You only need to be able to proof or convincingly show that you earned it legally and paid all potential US taxes that you had to pay. If you chose to bring it in cash, you need to tell customs when arriving (and again, be prepared to proof the legal sources). Wire transfer, cash in the suitcase, whatever you like. There is no tax for bringing the money, and the tax for making that money supposedly is already paid. Once the money is in the US, and earns more money, you will owe taxes on the gain (not on the capital itself, just on the amounts it increases by) I hope you understand that if you live in the US, and you have money anywhere in the world, you might need to report it to the IRS; and if your money makes interest anywhere in the world (including of course in India), you might be are required to pay US taxes on the gains. That is independent of your question; but if you don't do it, you are cheating the IRS, and they will ask this when you bring the money back. To explain the capital gains part of the question, non qualified stock options (NSOs) are always treated like earned income and have payroll taxes withheld. It's advantageous for the company to issue these because they can deduct them as expenses just as they do your salary. Articles talking about capital gains would probably be referring to incentive stock options (ISOs) or possibly even restricted stock units (RSUs). If you were granted the option to buy the stock and/or hold it for a period of time, then the stock options could be treated as capital gains, short-term gains if you held them for less than a year, and long-term gains if you held them for more than a year. This payment for your NSOs is exactly like a cash bonus. The withholding follows the same guidelines. You may wish to look at what this will mean for your annual salary and adjust your W-4 withholding up or down as appropriate depending on whether the 25% federal withholding rate is more or less than what you think your final marginal rate will be with this bonus included in your annual salary. "There is not a special rate for short-term capital gains.  Only long-term gains have a special rate.  Short-term gains are taxed at your ordinary-income rate (see here).  Hence if you're in the 25% bracket, your short-term gain would be taxed at 25%.  The IRA withdrawal, as you already mentioned, would be taxed at 25%, plus a 10% penalty, for 35% total.  Thus the bite on the IRA withdrawal is larger than that on a non-IRA withdrawal. As for the estimated tax issue, I don't think there will be a significant difference there.  The reason is that (traditional) IRA withdrawals count as ordinary taxable income (see here).  This means that, when you withdraw the funds from your IRA, you will increase your income.  If that increase pushes you too far beyond what your withholding is accounting for, then you owe estimated tax.  In other words, whether you get the money by selling stocks in a taxable account or by withdrawing them from an IRA, you still increase your taxable income, and thus potentially expose yourself to the estimated tax obligation. (In fact, there may be a difference.  As you note, you will pay tax at the capital gains rate on gains from selling in a taxable account.  But if you sell the stocks inside the IRA and withdraw, that is ordinary income.  However, since ordinary income is taxed at a higher rate than long-term capital gains, you will potentially pay more tax on the IRA withdrawal, since it will be taxed at the higher rate, if your gains are long-term rather than short term.  This is doubly true if you withdraw early, incurring the extra 10% penalty.  See this question for some more discussion of this issue.) In addition, I think you may be somewhat misunderstanding the nature of estimated tax.  The IRS will not ""ask"" you for a quarterly estimated tax when you sell stock.  The IRS does not monitor your activity and send you a bill each quarter.  They may indeed check whether your reported income jibes with info they received from your bank, etc., but they'll still do that regardless of whether you got that income by selling in a taxable account or withdrawing money from an IRA, because both of those increase your taxable income. Quarterly estimated tax is not an extra tax; it is just you paying your normal income tax over the course of the year instead of all at once.  If your withholdings will not cover enough of your tax liability, you must figure that out yourself and pay the estimated tax (see here); if you don't do so, you may be assessed a penalty.  It doesn't matter how you got the money; if your taxable income is too high relative to your withheld tax, then you have to pay the estimated tax.  Typically tax will be withheld from your IRA distribution, but if it's not withheld, you'll still owe it as estimated tax." No such account exists as capital gains aren't realized until holdings are sold. For example: OR  Both scenarios would result in you owing the appropriate taxes on a $40 gain from the dividends.   The $100 gain or $100 loss that isn't realized (you haven't sold the stock) isn't accounted for until the year of sale. I don't see a tag for United States, so I'm having to assume this is US taxes.  It doesn't matter what app you use, IRS trades are all calculated the same. First, you have to report each trade on a 8949 and from that the totals go into a schedule D.  Short term trades are stocks that you've kept exactly one year or less, long term trades are for 1 year + 1 day or more.  Trades where you sold a stock for a loss, then bought that stock back again under 30 days don't get to count as a loss.  This only affects realized capital gains and losses, you don't count fees. First, take all of your short term gains then offset them by all of your short term losses.  Do the same for long term gains and losses.  Short and long term gains are taxed at different rates.  You can deduct losses from short term to your long term and vice versa.  Then you can deduct the total losses up to $3000 (household, $1500 married, filing separately) per year on your regular income taxes or other dividend taxes.  If you have over $3000 in losses, then you need to carry that over to subsequent years. Edited per Dave's comments: thanks Dave Phil's answer is correct. Just to add to his response: Distributions are not taxable events -- you already paid your taxes, so you can take out $50k or $52k and the IRS is not concerned. You can simply write yourself a check for any amount you choose! To answer your specific question: to match your K1 losses and profit exactly, you could take out $50k. But that might leave the business strapped for cash. One way to decide how much to take out is to use your balance sheet. Look at your retained earnings (or just look at the business bank account balance), subtract however much cash you think you need to keep on hand for operations, and write yourself a check for the rest. All corporate gains are taxed at the same rate as corporate income, for the corporate entity, so this actually can be WORSE than the individual capital gains tax rates. There are a lot of things you can do with trading certain asset classes, like opening you up to like-kind re-investment tax perks, but I can't think of anything that helps with stocks. Also, in the US there is now a law against doing things solely to avoid tax if they have no other economic purpose. So be conscious about that, you'll need to be able to rationalize at least a thin excuse for why you jumped through all the hoops.