Should all "Transactions for which basis is not reported to the IRS and Term is Unknown" appear on a 1099-B statement with Box E checked?

[jstracy13]

From what I'm reading in TurboTax help, any transaction listed as "Transactions for which basis is not reported to the IRS and Term is Unknown" should generate a Form 8949 with Box E checked, separate from the Form 8949 with Box D checked for other stock sales. However, when I attempt to import my 1099-B, TT attempts to merge the (Docebo) Box E entry in with my Box D entries on the Capital Asset Sales Worksheet, and signals errors  because the Date Acquired, Cost Basis, and Holding Period aren't reported (as expected).

Additionally, the entry is completely missing from the Form 8949, i.e., no second copy for that transaction is created as I *think* it should. I have attempted to delete and re-import the 1099-B to no avail. I also noticed that after deleting and reimporting, my federal and state refunds both increased, so I'm concerned that there's something else off in this process.

[jstracy13]

I think that when I deleted both the 1099-DIV and 1099-B and reimported, it didn't bring the 1099-DIV back in, so that may be the source of the refund disparity. I'm trying a few things to test the theory.

That said, the original question about Form 8949 in this scenario remains.

[JamesG1]

Does your financial institution provide two IRS form 1099-B's, one for Box D, one for Box E?

If so, IRS form 1099-B reporting Box E may be reported by entering One by One information, correcting the missing information.

IRS form 1099-B reporting Box D may be reported by entering summary information. Create a .PDF of the IRS form 1099-B to upload into TurboTax Online.  Follow these steps. 

1. Down the left side of the screen, click Federal.
2. Down the left side of the screen, click Wages & Income.
3. Click the down arrow to the right of Investments and Savings.
4. Click to the right of Stocks, Cryptocurrency, Mutual Funds, Bonds, Other (1099-B).
5. Click Add investments.
6. On the Let's import your tax info screen, select Enter a different way.
7. On the OK, let's start with one investment type screen, select Stocks, Bonds, Mutual Funds, then Continue.
8. At the screen Which bank or brokerage, enter the information.  Click Continue.
9. Do these sales include any employee stock, enter No.
10. Do you have more than three sales, enter Yes.
11. Do these sales include any other types of investments, enter No.
12. Did you buy every investment listed, enter Yes.  Continue.
13. On the screen Now, choose how to enter your sales, select Sales section totals.  Select Continue.
14. At the screen Look for your sales on your 1099-B, select Continue.
15. You will now be able to enter the total proceeds (sales) and cost basis, along with the sales category. Refer to your IRS form 1099-B, IRS form 8949 and / or Schedule D Capital Gains and Losses for the amounts and category. When finished, select Continue
16. You can add additional sales totals by selecting the Add another sales total on the Review your sales section totals screen.
17. When completed, close the record and click Continue.
18.  At the screen Now, we'll help you upload your 1099-B since the IRS requires a copy, browse and select your document.  Select Continue.
19. When you upload your document, your filing instructions will not show that anything needs to be mailed in, and no IRS form 8453 will be generated.

IRS form 1099-B reporting Box E may be reported by entering One by One information, correcting the missing information.  Follow these steps.

1. Click Add investments.
2. On the Let's import your tax info screen, select Enter a different way.
3. On the OK, let's start with one investment type screen, select Stocks, Bonds, Mutual Funds, then Continue.
4. At the screen Which bank or brokerage, enter the information.  Click Continue.
5. Do these sales include any employee stock, enter No.
6. Do you have more than three sales, enter Yes.
7. Do these sales include any other types of investments, enter No.
8. Did you buy every investment listed, enter Yes.  Continue.
9. On the screen Now, choose how to enter your sales, select One by one.  Select Continue.
10. At the screen Look for your sales on your 1099-B, select Continue.
11. You will now be able to enter the transaction.  When finished, select Continue
12. You can add additional sales totals by selecting the Add another sale on the Review your sales screen.
13. When completed, close the record and click Continue.