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Last year I sold 100 shares of one of my stocks in ONE order. However, I didn't buy those shares at the same time. They were from multiple purchases at different times (around 7 times). In my 1099B form, Fidelity shows profits for each of the separate purchase, plus the total profit for the whole 100 shares.

So my question is when I file tax, do I report the sale of 100 shares as a single entry, OR do I have to report individual purchases separately, which will be very tedious.

Thanks in advance.

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You report each position separately. You do this on form 8949. 7 positions is nothing, it will take you 5 minutes.

There's a tip on form 8949 that says this, though:

For Part I (short term transactions):

Note. You may aggregate all short-term transactions reported on Form(s) 1099-B showing basis was reported to the IRS and for which no adjustments or codes are required. Enter the total directly on Schedule D, line 1a; you are not required to report these transactions on Form 8949 (see instructions).

For Part II (long term transactions):

Note. You may aggregate all long-term transactions reported on Form(s) 1099-B showing basis was reported to the IRS and for which no adjustments or codes are required. Enter the total directly on Schedule D, line 8a; you are not required to report these transactions on Form 8949 (see instructions).

If the 1099B in your case shows basis for each transaction as reported to the IRS - you're in luck, and don't have to type them all in separately.

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You can group your like-kind (same symbol, ST/LT) stock positions, just be sure that your totals match the total dollar amounts on the 1099. An inconsistency will possibly result in a letter from IRS to clarify.

So, if you sold the 100 shares, and they came from 7 different buys, list it once. The sell price and date is known, and for the buy price, add all the buys and put "Various" for the date.

If you have both long term and short term groups as part of those 7 buys, split them into two groups and list them separately.

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  • No, you cannot group them unless 1099B reports purchase price per position. This is plain wrong.
    – littleadv
    Commented Feb 23, 2014 at 1:12

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