Restricted Stock Grants - How to prepare tax return when you sell to cover taxes
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.
"I've bought ISO stock over they years -- in NYSE traded companies.  Every time I've done so, they've done what's called ""sell-to-cover"".  And the gubmint treats the difference between FMV and purchase price as if it's part of your salary.  And for me, they've sold some stock extra to pay estimated taxes. So, if I got this right...  20,000 shares at $3 costs you 60,000 to buy them.  In my sell-to-cover at 5 scenario: did I get that right?  Keeping only 4,000 shares out of 20,000 doesn't feel right.  Maybe because I've always sold at a much ratio between strike price and FMV. Note I made some assumptions:  first is that the company will sell some of the stock to pay the taxes for you.  Second is your marginal tax rate.  Before you do anything check these. Is there some reason to exercise immediately?  I'd wait, personally." "In this scenario the date of income is the date on which the contract has been signed, even if you received the actual money (settlement) later. Regardless of the NY special law for residency termination - that is the standard rule for recognition of income during a cash (not installments) sale. The fact that you got the actual money later doesn't matter, which is similar to selling stocks on a public exchange. When you sell stocks through your broker on a public exchange - you still recognize the income on the day of the sale, not on the day of the settlement. This is called ""the Constructive Receipt doctrine"". The IRS publication 538 has this to say about the constructive receipt: Constructive receipt.   Income is constructively received when an   amount is credited to your account or made available to you without   restriction. You need not have possession of it. If you authorize   someone to be your agent and receive income for you, you are   considered to have received it when your agent receives it. Income is   not constructively received if your control of its receipt is subject   to substantial restrictions or limitations. Once you signed the contract, the money has essentially been credited to your account with the counter-party, and unless they're bankrupt or otherwise insolvent - you have no restrictions over it. And also (more specifically for your case): You cannot hold checks or postpone taking possession of similar   property from one tax year to another to postpone paying tax on the   income. You must report the income in the year the property is   received or made available to you without restriction. Timing wire transfer is akin to holding and not depositing a check, from this perspective. So unless there was a restriction that was lifted after you moved out of New York, I doubt you can claim that you couldn't have received it before moving out, i.e.: you have, in fact, constructively received it." I can make that election to pay taxes now (even though they aren't vested) based on the dollar value at the time they are granted? That is correct. You must file the election with the IRS within 30 days after the grant (and then attach a copy to that year's tax return). would I not pay any taxes on the gains because I already claimed them as income? No, you claim income based on the grant value, the gains after that are your taxable capital gains. The difference is that if you don't use 83(b) election - that would not be capital gains, but rather ordinary salary income. what happens if I quit / get terminated after paying taxes on un-vested shares? Do I lose those taxes, or do I get it back in a refund next year? Or would it be a deduction next year? You lose these taxes. That's the risk you're taking. Generally 83(b) election is not very useful for RSUs of established public companies. You take a large risk of forfeited taxes to save the difference between capital gains and ordinary gains, which is not all that much. It is very useful when you're in a startup with valuations growing rapidly but stocks not yet publicly trading, which means that if you pay tax on vest you'll pay much more and won't have stocks to sell to cover for that, while the amounts you put at risk are relatively small. "Consider property taxes (school, municipal, county, etc.) summing to 10% of the property value.  So each year, another .02N is removed.  Assume the property value rises with inflation.  Allow for a 5% after inflation return on a 70/30 stock bond mix for N.   After inflation return.   Let's assume a 20% rate.  And let's bump the .05N after inflation to .07N before inflation.  Inflation is still taxable.   Result  Drop in value of investment funds due to purchase.   Return after inflation.   After-inflation return minus property taxes.   Taxes are on the return including inflation, so we'll assume .06N and a 20% rate (may be lower than that, but better safe than sorry).   Amount left.   If no property, you would have .036N to live on after taxes.  But with the property, that drops to .008N.  Given the constraints of the problem, .008N could be anywhere from $8k to $80k.   So if we ignore housing, can you live on $8k a year?  If so, then no problem.  If not, then you need to constrain N more or make do with less house.   On the bright side, you don't have to pay rent out of the .008N.  You still need housing out of the .036N without the house.   These formulas should be considered examples.  I don't know how much your property taxes might be.  Nor do I know how much you'll pay in taxes.  Heck, I don't know that you'll average a 5% return after inflation.  You may have to put some of the money into cash equivalents with negligible return.  But this should allow you to research more what your situation really is.   If we set returns to 3.5% after inflation and 2.4% after inflation and taxes, that changes the numbers slightly but importantly.  The ""no house"" number becomes .024N.  The ""with house"" number becomes  So that's $24,000 (which needs to include rent) versus -$800 (no rent needed).  There is not enough money in that plan to have any remainder to live on in the ""with house"" option.  Given the constraints for N and these assumptions about returns, you would be $800 to $8000 short every year.   This continues to assume that property taxes are 10% of the property value annually.  Lower property taxes would of course make this better.  Higher property taxes would be even less feasible.   When comparing to people with homes, remember the option of selling the home.  If you sell your .2N home for .2N and buy a .08N condo instead, that's not just .12N more that is invested.  You'll also have less tied up with property taxes.  It's a lot easier to live on $20k than $8k.   Or do a reverse mortgage where the lender pays the property taxes.  You'll get some more savings up front, have a place to live while you're alive, and save money annually.   There are options with a house that you don't have without one." "Summary of accepted answer: Your ""loss"" will not count as a loss (to the IRS).  Which means no tax deduction for a ""short-term capital loss"" (on that sale). Instead, the IRS simply pretends like you had paid less for the stock to begin with." "Yes, you can do that, but you have to have the stocks issued in your name (stocks that you're holding through your broker are issued in ""street name"" to your broker). If you have a physical stock certificate issued in your name - you just endorse it like you would endorse a check and transfer the ownership. If the stocks don't physically exist - you let the stock registrar know that the ownership has been transferred to someone else. As to the price - the company doesn't care much about the price of private sales, but the taxing agency will. In the US, for example, you report such a transaction as either a gift (IRS form 709), if the transaction was at a price significantly lower than the FMV (or significantly higher, on the other end), or a sale (IRS form 1040, schedule D) if the transaction was at FMV." At the end of each calendar year the mutual fund company will send you a 1099 form. It will tell you and the IRS what your account earned. You will see boxes for: You will end up paying taxes on these, unless the fund is part of a 401K or IRA. These taxes will be due even if you never sold any shares. They are due even if it was a bad year and the value of your account went down. Most if not all states will levy an income tax yon your dividends and capital gains each year. When you sell your shares you may also owe income taxes if you made a profit. The actual taxes due is a more complex calculation due to long term vs short term, and what other gains or losses you have. Partial sales also take into account which shares are sold. No. There is no asset associated with your short position, so there's nothing to gift. The short position in the stock is purely a liability. When you note that you have a profit in the position, what you mean is that the cash you made when you shorted the stock is more than enough to cover the short position. The only asset in this picture, then, is the cash you made when you entered the short position.