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

[tonybrummel]

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?  

[TomYoung · Accepted solution]

"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

[tonybrummel]

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?

[TomYoung]

If you're doing this correctly you should land on a page titled ""Stock Option Lot Summary."  On that page is a button titled "Add Another Lot".  You keep adding another lot until you're done.  If instead of clicking on "Add Another Lot" on that page you click "done" then you're placed on a page titled "Add Another Lot" showing how many shares are unaccounted for in your sale and asking "Do you want to enter another lot?"

If you're not seeing that then I'd guess you're in the wrong place.  Delete and start over.

[tonybrummel]

I think I missed the question about exercising the shares at multiple times. Now I'm seeing lots. Thank you.

[tkbirdie]

I had same problem and this was helpful.. But I also get to the Enter Your Sale Information page and it limits the number of shares.  I have more than the 99,000 it will allow.   So my total number of shares is larger than this will allow and then won't match my 1099-B.  Any insights how to handle that would be appreciated.  

[Tax2019Pay]

Hi, Tom:

I have tried to ask the question about non-qualified stock option exercise on this board but did not get a clear response; mostly due to the way that I have asked questions.  Reading your responses to various questions, you seem to be the expert that I am looking for.  So thank you in advance for educating me on this topics.

Here is the background.  I had 1000 shares of company stock option granted on July 15, 2020 and vested on July 15, 2021.  I exercised the options in 100 share lot x 10 times between Jul 15, 2021 (each time with immediate sale for cash).  In January 2022, I received a W2 (with box12a showing "V")  from the company for the gain; and I also received a consolidated 1099B with a summary of the total proceed and cost base, and as well as detailed information for each of 10 option exercises.   These option exercises/sales were reported as short term covered without the need for any adjustment.  Since the 1000 shares of option came from the same lot, so the cost base was the same.

I entered the W2 information and 1099B information as shown in these tax forms.  But I need to add the W-2 amount to the cost base number on 1099B to avoid being double taxed.  My problem is that I do not know how to do that to make it clear to the IRS.  

Am I allowed to summarize all these 10 option exercises/sales into one consolidated proceed and one consolidated cost base, or do I have to enter one option exercise/sale at the time and enter 10 times?  If I am allowed to summarize, how do I add the cost base from W2?  In the summary mode, there is nothing in TurboTax allowing me to do the cost base adjustment - I guess that I could just add the W2 amount to the 1099B cost base - but wouldn't IRS be confused by this?  If I enter one option exercise/sale at a time, TurboTax will ask me if it is an employer stock option and lead me to run through a worksheet to do the adjustment but that is 10 worksheets to go through.  

I am trying to find a best way to do it clearly and in a most simplified manner.  Thanks in advance.

[RobertB4444]

The IRS has already received a copy of both your 1099-B and your W-2.  You are adding the number to your cost basis that they know should be added to the basis.  

As far as how to enter the sale in TurboTax it's kind of dealer's choice.  You can divide the amount on your W-2 by 10 and enter it into each transaction or enter the whole thing in the summary section.  Either way it still adds up to the right total.

[Tax2019Pay]

Thanks.  So to confirm, I can (1)  enter in summary without having to list individual transactions, (2) adjust the 1099B cost base by adding the W2 box 1 stock transaction amount to the 1099 base, and (3) since these transactions were all short term covered without the need for adjustment, I do not have to mail in Form 8949 to IRS after eFile in Turbo Tax.   Am I correct with the above?

[Tax2019Pay]

For exercise non-qualified stock options - same lot / same cost base, short term gain covered, no adjustment needed, but exercised multiple times.  When does one need to attach 1099B or send in Form 8949?  I thought that the brokerage firm should send the 1099B to the IRS, and in my case, Form 1099B is even combined with Form 8949 showing the multiple exercises of the same option grant lot.  So my thinking is that under this scenario, one does not need to attach 1099B or send in Form 8949 to the IRS.  Am I wrong here?

[GeorgeM777]

Yes, you do not need to attach Form 1099-B to your return; however, if you are e-filing your return, Form 1099-B will not be e-filed along with, or otherwise attached, to your return.  To follow-up on the comments from @RobertB4444, your brokerage firm has already filed your 1099-B with the IRS, probably on or about the time that such form was made available to you.  

Generally, Form 8949 allows you and the IRS to reconcile amounts that were reported to you and the IRS on Forms 1099-B or 1099-S (or substitute statements) with the amounts you report on your return. 

According to the IRS, Form 8949 isn't required for certain transactions. You may be able to aggregate those transactions and report them directly on either line 1a (for short-term transactions) or line 8a (for long-term transactions) of Schedule D. This option applies only to transactions (other than sales of collectibles) for which:

• You received a Form 1099-B (or substitute statement) that shows basis was reported to the IRS and doesn't show any adjustments in box 1f or 1g;
• The Ordinary box in box 2 isn’t checked;
• You don't need to make any adjustments to the basis or type of gain (or loss) reported on Form 1099-B (or substitute statement), or to your gain (or loss); and
• You aren’t electing to defer income due to an investment in a QOF (Qualified Opportunity Fund) and aren’t terminating deferral from an investment in a QOF.

Thus, if the above exceptions apply in your case, then Form 8949 will not be necessary and you can report your transactions in the aggregate on Schedule D.  

@Tax2019Pay