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My suggestion is to NOT use the RSU step by step interview to report these sale. That interview confuses lots of people and there is no valid "income tax reporting" reason that you need to use that particular interview. You can report the sale as a simple sale of plain-vanilla stock, stock that's no different than a stock you bought through your broker.
But to answer the question you've posed in your example, you'd say 50 shares vested on the 50 share sale and 150 shares vested on the 150 share sale. That "withheld for taxes" box can be left blank. But if you do end up using the RSU step by step interview make sure you go all the way to the end of the "Stocks, Mutual Funds, Bonds, Other" interview. Don't just stop when you finish entering the trades. There's a page that comes up asking if the compensation created by the vestings of the RSU's agrees to your W-2.
Here's the information you need to understand so you don't consider yourself a "stock imbecile."
Here's what makes reporting the sale of stock acquired via an RSU just slightly puzzling: starting in 2014 brokers need only report the "out of pocket" cost of of stock that's been acquired through an employer stock incentive program. Since you pay nothing "out of pocket" when an RSU vests, the brokers typically report a basis of $0 when you sell the stock. If you report the sale exactly like it reads on the 1099-B then you end up reporting income twice: once as "compensation" income on the W-2 when the stock vests, and then as an overstatement of "gain" (or understatement of "loss) when you report the sale.
So clearly what you need to do is to enter the sale in TurboTax just like the broker reported it, then adjust the basis from $0 to the correct amount.
To do this you simply report the sale as a plain-vanilla stock, entering the details off the 1099-B just as it reads. Then click the blue "I'll enter additional info on my own" button. On the next page enter the correct basis in the "Corrected cost basis" box. And the correct basis is simply (# of shares sold) x (per share basis for that lot). Much easier then using the RSU step by step process.
If you didn't get a 1099-B for a sale of some of those shares, (brokers aren't required to prepare 1099-B's for a "same day" sale, but they do need to prepare a "statement" with the same information), you can enter those sales, too, though you don't have to.
In this case you'd tell TurboTax that no 1099-B was received, identify that what you're selling is simply "stock", enter a description the amount of proceeds, and the date of sale. Tell TurboTax you "bought" the stock, your "date purchased" is the vesting date, and then enter your purchase price which, again is (# of shares sold) x (per share basis for that lot).
Tom Young
My suggestion is to NOT use the RSU step by step interview to report these sale. That interview confuses lots of people and there is no valid "income tax reporting" reason that you need to use that particular interview. You can report the sale as a simple sale of plain-vanilla stock, stock that's no different than a stock you bought through your broker.
But to answer the question you've posed in your example, you'd say 50 shares vested on the 50 share sale and 150 shares vested on the 150 share sale. That "withheld for taxes" box can be left blank. But if you do end up using the RSU step by step interview make sure you go all the way to the end of the "Stocks, Mutual Funds, Bonds, Other" interview. Don't just stop when you finish entering the trades. There's a page that comes up asking if the compensation created by the vestings of the RSU's agrees to your W-2.
Here's the information you need to understand so you don't consider yourself a "stock imbecile."
Here's what makes reporting the sale of stock acquired via an RSU just slightly puzzling: starting in 2014 brokers need only report the "out of pocket" cost of of stock that's been acquired through an employer stock incentive program. Since you pay nothing "out of pocket" when an RSU vests, the brokers typically report a basis of $0 when you sell the stock. If you report the sale exactly like it reads on the 1099-B then you end up reporting income twice: once as "compensation" income on the W-2 when the stock vests, and then as an overstatement of "gain" (or understatement of "loss) when you report the sale.
So clearly what you need to do is to enter the sale in TurboTax just like the broker reported it, then adjust the basis from $0 to the correct amount.
To do this you simply report the sale as a plain-vanilla stock, entering the details off the 1099-B just as it reads. Then click the blue "I'll enter additional info on my own" button. On the next page enter the correct basis in the "Corrected cost basis" box. And the correct basis is simply (# of shares sold) x (per share basis for that lot). Much easier then using the RSU step by step process.
If you didn't get a 1099-B for a sale of some of those shares, (brokers aren't required to prepare 1099-B's for a "same day" sale, but they do need to prepare a "statement" with the same information), you can enter those sales, too, though you don't have to.
In this case you'd tell TurboTax that no 1099-B was received, identify that what you're selling is simply "stock", enter a description the amount of proceeds, and the date of sale. Tell TurboTax you "bought" the stock, your "date purchased" is the vesting date, and then enter your purchase price which, again is (# of shares sold) x (per share basis for that lot).
Tom Young
The grant itself has nothing to do with the valuation. Each vesting sets the price for the gross number of shares received in that vesting. So each vesting is a lot and each lot has a per share basis that's the same as the per share "fair market value" used by the employer to calculate the compensation that's going to be reported for that lot.
Broadly speaking your basis is the same as that stock's "price" on the day of vesting, but of course a stock's price varies during any given trading day. Your employer picks a price to use - it might be the same price you sold the stock at, or it might not be - so the "most accurate" basis number to use is the same one your employer used.
If you ever end up holding some of these stocks for many years and lose all your paperwork on the vesting, but remember the vesting date, looking up the stock's closing price on that date would be "close enough."
Your comment about "already entered the number of shares withheld to pay taxes" suggests to me that you are using, or used, the RSU step by step process as that's the ONLY place in TurboTax that asks that question. Although I guess you could be referring to entering the sales of shares sold "for taxes"? But then you also mention "the same page where I enter the corrected cost basis" and suggest that you're using the same method I recommended to mrbusto71. You can't use both methods, the RSU step by step or the "normal" 1099-B entry with basis correction, you only use one or the other.
If you are using the RSU step by step method, entering the shares withheld "for taxes" does absolutely nothing, except lower the number of share available for sale "not for taxes". That is, you get no credit for "taxes withheld" on your income tax return because you told TurboTax the number of shares withheld for taxes.
When entering the sale of these shares using the regular "1099-B" interview - where you simply transcribe numbers of your paper 1099-B into a TurboTax screen that uses the same box numbers - you only enter taxes withheld if those taxes are actually showing up on the "official" 1099-B. Taxes withheld are normally reported on the W-2.
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