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Aleksandr
Level 3

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

Hello!I have a complicated tax case connected to stock market(E*Trade broker).
1) I have a lot of transactions last year(2020) - more then 10.000 (ten thousands).All of them - "short term".
2) I have total sales more then $10.000.000(ten million)
3) I have a lot of wash sales transactions (more then thousand)
4) Among all transactions there are ESPP and RSU sale transactions that require cost basis adjustment.
5) I've got dividends (~$5000)

I know that TurboTax has limitations for imported transaction from each broker (max 2500),
limitation on "total sales sum" (max $10.000.000).For all adjusted transactions(wash sales+ESPP+RSU) I should have details in form 8949 (it should have hundreds of pages - so it's not impossible to send IRS printed form) .

Taking into account all above, what the best approach you can suggest to proper file my taxes in TurboTax?
I'm ready to pay some extra money to ease for myself the process of filing.(for example for some auxiliary specialized software)

13 Replies
DaveF1006
Employee Tax Expert

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

You can enter summary transactions into your Turbo Tax program that will reduce the number of entries made Here is a step by step instruction on how to report summary transactions in Turbo Tax found in this link.

 

How to enter a summary in lieu of individual transactions

Your brokerage statements should include a summary of your transactions, grouped by sales category, for example, "Box A short-term covered" or "Box D long-term covered." You'll enter the summary info instead of each individual transaction.

  1. Open or continue your return (if it's not already open) and search inside TurboTax for the phrase stock sales.
  2. Select the Jump to link in the search results. if you use Turbo Tax online, you will go to federal>wages and income>investment income>show more
  3. Stocks, Mutual Funds, Bonds, Other (1099-B)
  4. Answer Yes to both Did you sell stocks, mutual funds, bonds, or other investments? and Did or will you receive a 1099-B form or brokerage statement for these sales?
    • If you land on Here are all your 1099-B sales, select Add sales from a different brokerage. Then answer Yes to Did or will you receive a 1099-B form or brokerage statement for these sales?
  5. When asked how you want to enter your 1099-B, select I'll type it in myself.
  6. Select or enter your brokerage on the next screen and continue.
  7. On the following screen (Tell us about...), answer the questions until you reach the next screen. Select the second option, Let's enter a summary instead, and select Continue.
  8. You'll now be able to enter the total proceeds (sales) and cost basis, along with the sales category. Refer to your 1099-B for the amounts and category. When finished, select Continue
  9. Once you are done, you will be able to efile your return but it will give you instructions to mail in a copy of your 1099-B to the IRS.  Turbo Tax will provide you with complete mailing instructions.

 

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Aleksandr
Level 3

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

Unfortunately this advise will NOT work for my case - it's only applicable to the case where no any adjustments are required , but I have wash sales+ESPPs sales - they are all "Box A" transactions that need to be adjusted.
OR I should mail printed hardcopy of form 8949 with detailed transactions to IRS - it should be many hundreds of pages...this in insane to send IRS big shoe box with paper.
Another issue - TurboTax has limitation on "total sales sum" - max $10.000.000, but I have more then $10.000.000.

DaveF1006
Employee Tax Expert

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

it depends. Do you have a wash sale transaction with each trade? Can you consolidate some of the transactions that have no wash sale information in them?

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Aleksandr
Level 3

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

Of course not: only ~10% of transactions are wash sales, ~90% - not. But how to consolidate them? Manually go through  all 10000 transactions and pick only those without wash sales? It's unreal.

ssurana
New Member

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

I also have a similar case. The issue is the sum of the total sales for my case also exceeds $10,000,000. Due to this even if I want to enter just the summary I can't.

How can this be solved?

fanfare
Level 15

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

There is tax software that lets you attach a PDF of your consolidated 1099-B when you e-File.

This obviates mailing paper details to IRS in Austin TX.

 

Hint: it's not TurboTax.

Aleksandr
Level 3

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

I'm going to use the solution below for my case, but I want to hear 2nd opinion.
Solution is: I arbitrarily divide my "totals" from "Covered Short−Term Gains or Losses on Net Proceeds" of 1099B  for 2 huge individual sales - each of them will be less then "10,000,000.00" (this division I make arbitrarily because I's hard to take out  from 10000 transactions  only "wash sale" sales).
For one of them (let's say sale "AAA") I make "totals" wash  sale adjustment from 1099B.
The other (let's say sale "BBB") can be just ordinary sale without any adjustments and may be with "0" gain - just to have sum of these 2 sales to match  the "totals" numbers of my 1099B.
The question IS: does it make sense to set adjustment code "M" for sale "BBB" to declare it as "aggregated of multiply sales without adjustments"?
Per my understanding in any of case above (or with sale "BBB" as "regular" or as "aggregated") I don't need to mail IRS the "big shoe box" of paper (more then 5000 pages of my 1099B).

JohnB5677
Expert Alumni

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

You do not have to be that complicated, but if you want to keep a clear distinction you can split the wash sales from the other transactions.

 

Your brokerage statements should include a summary of your transactions, grouped by sales category.

 

There are seven possible "Box" designations that indicate the holding period (Long/Short Term) and the reporting status.  These are the only ones you have to summarize. If you want to manually enter your 1099-B as the summaries.

 

  1. Tell us about your 1099-B sales for this  account
  2. Answer the questions
  3. Since you have more than a few  sales, we recommend entering sales section totals
  4. Continue
  5. Before entering sales section totals, take a moment to find them on your 1099-B
  6. Continue
  7. Now, we'll enter one sales section total on your  1099-B
  8. Use the drop down menu to select the correct designation.

 

Code A. This code indicates a short-term transaction for which the cost or other basis is being reported to the IRS.

 

Code B. This code indicates a short-term transaction for which the cost or other basis is not being reported to the IRS.  

 

Box C. Report on a Part I with box C checked all short-term transactions for which you can't check box A or B because you didn't receive a Form 1099-B (or substitute statement). 

 

Code D. This code indicates a long-term transaction for which the cost or other basis is being reported to the IRS.

  

Code E. This code indicates a long-term transaction for which the cost or other basis is not being reported to the IRS.  

 

Box F.  Report on a Part II with box F checked all long-term transactions for which you can't check box D or E because you didn't receive a Form 1099-B (or substitute statement).

 

Code X. Use this code to report a transaction if you cannot determine whether the recipient should check box B or box E on Form 8949 because the holding period is unknown.

 

If you post them under these designations you can simply mail the summary sheets and not the entire shoe box.

 

 

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Aleksandr
Level 3

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

1) I'm not able to enter "summary of your transactions" for "Code A" - I have gross numbers MORE then "10,000,000.00". TurboTax DOESN'T allow to enter numbers more then "10,000,000.00" .
2) There is 2nd reason I'm not able to enter "summary of your transactions" for "Code A" :
     I have  ESPP sales under "Code A" that require manual adjustment of  cost basis.
3) This is the first time ever I hear that if you enter "summaries" by categories "you can simply mail the summary sheets". It's doesn't make sense. IRS wants some kind of "statement of detail".

fanfare
Level 15

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

@Aleksandr 

 

IRS Exception: if you summarize Category A or Category D, Form 8949 is not needed for transactions without adjustments. No mailing is necessary.

---
As an active investor, be aware that your category Box A or Box D sales without adjustments do not require Form 8949, so there is no reason to import or key in those transactions.
Instead use the "enter a summary" option to put your numbers on Schedule D Line 1a or Line 8a.
--
If you have wash sales, it gets more complicated since those adjusted transactions have to be itemized on Form 8949 and the summary totals adjusted accordingly.

---

In your situation, that exception is not going to help much.

 

Again, I advise going with the other tax software that will let you attach your 1099-B PDF when you e-File.

You can even separate it into multiple PDF files if one PDF is too huge.

fanfare
Level 15

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

complain to your broker, ask them why the won't give you two selectable reports for import:
transactions with adjustments and,
transaction without adjustments.

Aleksandr
Level 3

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

Yes, I have a HUGE amount of wash sales ,so even  mailing only them takes a lot of paper. Not an option!
So the only way for me - summarize Category A and apply total amount of "wash sales" to this "summary total".
After that I have 3 options:
1) Find the way how to attach 1099B PDF in TurboTax.
2) Use another tax software that allows to attach 1099B PDF.
3) Use the way I described above - enter the summary of Category A not as a "summary" but just as single huge transaction with wash sale adjustment.It just should correspond all Category A "totals" data from my 1099B.

Fortunately IRS gave  us an extra month.

fanfare
Level 15

Complicated tax case with stock market. More than 10.000 transactions, "total sales" more then $10.000.000, a lot of wash sales, RSUs+ESPP sold, dividends. Is TT still able handle such a case?

If you use option 3)

the grand sub-totals will appear on Schedule D line 1b. e-Filed Form 8949 will say "see attached".

TorboTax supports this on the summarizing page.

That's also the way you do option 1), if available.

 

If you can separate out the transactions with adjustments into PDF pages,

that's all you have to mail to the IRS if you are mailing details.

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