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How do I enter multiple sales for a single 1099-B?

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June 7, 2019
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I got a single 1099-B from my employer that shows the TOTAL for ISO stock I sold. However, I sold multiple lots acquired over several years and they are all different sales as the basis and gain are different for each.

In TurboTax (Premiere) when I say I got a 1099-B then it tries to use the TOTAL (from the 1099-B line 1d "proceeds") for EACH sale I enter. I don't see a way to say that the 1099-B has totals on it -- but then add individual stock sales that will eventually add up to that total. (my 1099-b does NOT list individual transactions - I have all the info for tracking basis in Excel). I have over a dozen sales and each one contains multiple lots. It's unclear how to do this. I've never had trouble in the past but I've never received a 1099-B either so that must be something new.

I determined that if I say "No" to "Did you get a 1099-B for this sale?", then I can go ahead and enter each sale. Once I'm done, all the math will be correct but there will be no 1099-B attached to my return in Turbo Tax. Is this the way to go in cases like mine?

TurboTax Premier Windows

Best answer by TomYoung

"I got a single 1099-B from my employer that shows the TOTAL for ISO stock I sold. However, I sold multiple lots acquired over several years and they are all different sales as the basis and gain are different for each."

Well, no. You have one sale, it just happens that that one sale comprises several lots of stock. And you certainly can tell TurboTax that you got a 1099-B and report the sale correctly.

There are several ways of attacking this. I'm assuming that these are qualified sales and/or disqualified sales where the compensation income is reported on your W-2.

Usually I don't recommend using the ISO step by step interview except in the case of stocks sold via an ISO. Ordinarily I'd say simply use the TurboTax default 1099-B input form, enter "various" in the date acquired field and then enter the correct basis sum in the cost field. (If some sales are short term and some long term then you break that sale into two parts and report each part accordingly.) But since you obviously did not sell all your ISO shares in the year you acquired them you should have used the "ISO Exercise and Hold" interview each year to report the unsold shares for purposes of AMT. That means that when you finally do sell those shares you need to report a different basis for AMT purposes than for "regular" tax, and using the ISO step by step interview makes the needed adjustment for you.

So, tell TurboTax you got a 1099-B, and tell TurboTax you'll enter one sale at a time. On the TurboTax "Tell us about your [Broker Name] 1099-B" page enter the 1099-B exactly as it reads. You can put "various" in the date of acquisition box. Then click the "Guide me step by step" blue box, tick the "I have sales from an Employee Stock Plan..." bubble and specify "ISO." You'll tell TT that you sold in 2017 shares acquired in a prior year, tell TT then total number of shares sold, and then on the page "How Did You Buy the Shares You Sold?" page tick the "At different times (multiple lots)" bubble.

The following interview will allow you to enter information on a lot-by-lot basis.

Tom Young

T

TomYoungAnswer

Employee

"I got a single 1099-B from my employer that shows the TOTAL for ISO stock I sold. However, I sold multiple lots acquired over several years and they are all different sales as the basis and gain are different for each."

Well, no. You have one sale, it just happens that that one sale comprises several lots of stock. And you certainly can tell TurboTax that you got a 1099-B and report the sale correctly.

There are several ways of attacking this. I'm assuming that these are qualified sales and/or disqualified sales where the compensation income is reported on your W-2.

Usually I don't recommend using the ISO step by step interview except in the case of stocks sold via an ISO. Ordinarily I'd say simply use the TurboTax default 1099-B input form, enter "various" in the date acquired field and then enter the correct basis sum in the cost field. (If some sales are short term and some long term then you break that sale into two parts and report each part accordingly.) But since you obviously did not sell all your ISO shares in the year you acquired them you should have used the "ISO Exercise and Hold" interview each year to report the unsold shares for purposes of AMT. That means that when you finally do sell those shares you need to report a different basis for AMT purposes than for "regular" tax, and using the ISO step by step interview makes the needed adjustment for you.

So, tell TurboTax you got a 1099-B, and tell TurboTax you'll enter one sale at a time. On the TurboTax "Tell us about your [Broker Name] 1099-B" page enter the 1099-B exactly as it reads. You can put "various" in the date of acquisition box. Then click the "Guide me step by step" blue box, tick the "I have sales from an Employee Stock Plan..." bubble and specify "ISO." You'll tell TT that you sold in 2017 shares acquired in a prior year, tell TT then total number of shares sold, and then on the page "How Did You Buy the Shares You Sold?" page tick the "At different times (multiple lots)" bubble.

The following interview will allow you to enter information on a lot-by-lot basis.

Tom Young

T

tonybrummelAuthor

That flow start out ok but it seems to go south (but maybe all is well?). After I enter the first sale (and acquisition info) using the step by step, I get a summary that shows the net sales price from the 1099 and then this single sale which is a fraction of the total. So the gain is wrong. No biggie, I have more to enter I think but then when I continue I'm returned to the 1099 screen titled "Sale #1" where it has replaced my values with 'see step by step'. I'm not sure now if I'm supposed to click 'Guide me step by step' again or click Done. I was never asked if this was a single lot I was entering - it appears to be treating my entries and the whole sale (not asking me if I have multiple lots that add up to the total). If I click Done then I'm asked if there was another Sale. As you said, it was really all one sale - just many lots so this seems wrong. However, maybe that's what I need to do -- say "Yes" I have another sale to enter?