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"Those ESSP and RSU were granted more than 10 years ago."
So clearly you have a sale reported to you on a 1099-B as noncovered.
" I know portion of granted RSU shares were traded to pay tax at the time it was vested."
COMPLETELY AD UTTERLY IRRELEVANT. Put that out of your mind.
There's no problem at all with reporting that sale as 200 shares and 300 shares, with the same date of course and the proceeds split properly.
The sale of the RSU shares is dead simple. You report the sale and simply enter the correct basis. The correct basis for each lot sold, stated as a "per share" number, is the per share "fair market value" of the stock used by your employer to calculate the compensation created by the vesting. So, for example, if 50 of those 200 shares vested on April 1, 2009 and the per share "fair market value" used by you employer was $20 per share then those shares contributed a basis to your 200 share trade of (50 x $20) #1,000. You just tote up the numbers of the various lots and enter that as the basis for the 200 shares. (Make sure you prepare a paper copy of your analysis and staple it to a paper copy of your "as filed" income tax return, just in case the IRS ever asks "how'd you come up with that basis?").
The sale of the ESPP shares needs a little more work. Although the sales of these shares are clearly "qualified" sales - sold at least 2 years after the grant date and 1 year after the date of acquisition - those sales CAN create reportable compensation income and that compensation income and that compensation income gets added to your "out of pocket" (discounted) price in calculating gain on sale. The easiest way of dealing with this is to use the ESPP "guide me step by step" process, entering your Form 3922 information and letting TurboTax handle the calculations. Be sure to go to the very bitter end of the "Stocks, Mutual Funds, Bonds, Other" interview. Don't simply stop when you are finished entering your trade information. Eventually you'll get to a page titled "Your Employee Stock Plan Results" where you'll be asked if the compensation TurboTax has calculated has been included on your W-2. You'll answer "No" and TurboTax will make the needed entry.
Tom Young
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