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Subject:  Re: 1099 Tactical Question Date:  1/21/2013  3:07 PM
Author:  TMFPMarti Number:  117480 of 132781

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).

How? With relatively few exceptions, 1099-B's don't report gain/loss. Don't confuse the "supplemental" information included with your 1099 package with what gets sent to the IRS and, more importantly, what would constitute proof in an audit.

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.

Sell, yes. Buy, see above.

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?


When basis reporting on the 1099-B became future law I warned that I personally wouldn't trust brokers to get it right and urged people not to change anything in their recordkeeping. That opinion hasn't changed.

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?

If you still have the records of that exchange I think you'll find that symbol reporting had nothing to do with the problem. As Peter noted, what the IRS really cares about is the totals.

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