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Do at least one entry for each sale shown on the 1099-B. If you purchased what was sold on more than one purchase date you can combine purchases and use "various" for the date. You must still separate between long- and short-term, though.

With one exception, all the lots of a sell order were executed on the same day, and all the lots of a buy order were executed on the same day (I may have a wash sale on one equity, but the 1099 should make that clear, too). It sounds like, then, that you're anticipating the 1099 to aggregate the various lots of a single buy/sell order into one line on the 1099.

The exception is some several-year-old stock shares acquired through my company's ESPP which were sold via a single sell order this year. The acquisition dates of these shares are unknown to my broker, as when I left that company, I transferred the shares from the company's ESPP plan manager to my broker. If I use an acquisition date of "various," how will I justify a claim of long-term for the cap gain? Is this just the same record-keeping drill that I'd have to do (and have done) to justify claims of explicit acquisition dates?

I use symbols.

I asked because the last time I used symbols, I got a letter from the IRS saying I'd under-reported my stock transactions, compared to the 1099s they'd received, and would I please send them a large (compared to my coin purse) chunk of money, plus interest and penalties? That was straightforwardly corrected (that record-keeping, again) by explaining where on the tax forms I'd sent them they could find my stock transactions and how they lined up with the 1099s we'd both received. But I don't need those heart-stopper letters.

Eric Hines
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