Investors & landlords

While maybe not the ideal solution, if you have the paper copy of your account you can enter the data manually as there are workarounds for all the information necessary to enter.

The 1099-B should guide you on what the treatment will be for including the trades on your return.  Generally your 1099-B should show the caption for the type of trade that it was - Short-term covered with basis reported to the IRS, Short-term not covered, Long-term covered, Long-term not covered.  Each section of the 1099-B needs to be entered separately.  You are allowed to combine transactions as one provided they are from the SAME grouping.  You enter the transactions in the Investment section of TurboTax as follows:

1. On the left side of your TurboTax screen, click on Wages & Income
2. Scroll down to "Investments & Savings" and click show more or edit/add
3. Click on "Add Investments"
4. Best thing to do here in my opinion is to click on "Enter a different way"
5. Click on the box for Stocks, Bonds, Mutual Funds and then continue
6. Enter the brokerage name at the top and the account number and Payer's EIN if you so choose (not required)
7. Answer the questions on the next page, which are normally, but not always, no, no (in this case even if it is more), no, and yes.
8. You can answer one by one and enter each group separately; if you answer yes you will will need to upload a pdf of your statement.
9. If your grouping has multiple sales, when you are asked the date acquired, click on something other than a date and choose various
10. Follow the remaining instructions and choices.  Whichever way you answer you will receive additional instructions.

Maybe not ideal as everyone would prefer to just have the upload perfect but if you are in a rush to file your return the above should assist.

@mprev 

@spq838