USAA 1099 brokerage tax statements are not available for import but in a PDF file. How do I upload a PDF file into Turbo Tax?

From time to time the broker's format is not compatible with TurboTax.

If you only have a few trades you can post them manually.                                                              

Income & Expenses

1. Scroll to Stocks, Mutual Funds, Bonds, Other
2. Answer Yes to Did you sell stocks, mutual funds, bonds, or other investments in 2020?
3. On the OK, what type of investments did you sell? screen, select Stock, Bonds, Mutual Funds. Then select Continue.
4. From here, you can import or manually enter your 1099-B.
5. Answer the questions about your sales. Choose to Enter sales one by one when asked.
6. On the Now, we'll enter one sale on your 1099-B screen, enter your info.

However, if there are more than a few you can quickly enter this manually also. 

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.

1. Open or continue your return (if it's not already open) and search inside TurboTax for the phrase stock sales.

1. Select the Jump to link in the search results.
2. 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?
3. 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?
4. When asked how you want to enter your 1099-B, select I'll type it in myself.
5. Select or enter your brokerage on the next screen and continue.
6. 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.
7. 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.

1. When you are done, you'll eventually come to the Here's a summary of your broker sales screen where you can edit, delete, or enter more sales.

You will have to mail a copy of your 1099-B to the IRS.  TurboTax will produce a Form 8453. You print the Form 8453 and attach the brokerage statement(s) to it. 

John - your answer was most helpful and solved my question.  Turbo Tax has a feature where I could upload the PDF and they will send it to the IRS for me.  Thank you.