Skip to main content
Message Font: Serif | Sans-Serif
No. of Recommendations: 1
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.

Rule Your Retirement Home Fool
Print the post  


In accordance with IRS Circular 230, you cannot use the contents of any post on The Motley Fool's message boards to avoid tax-related penalties under the Internal Revenue Code or applicable state or local tax law provisions.
What was Your Dumbest Investment?
Share it with us -- and learn from others' stories of flubs.
When Life Gives You Lemons
We all have had hardships and made poor decisions. The important thing is how we respond and grow. Read the story of a Fool who started from nothing, and looks to gain everything.
Contact Us
Contact Customer Service and other Fool departments here.
Work for Fools?
Winner of the Washingtonian great places to work, and Glassdoor #1 Company to Work For 2015! Have access to all of TMF's online and email products for FREE, and be paid for your contributions to TMF! Click the link and start your Fool career.