topic How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax? in Get your taxes done using TurboTax

How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

wt taxpayer — Sat, 13 Mar 2021 15:45:24 GMT

Brokerage firm USAA switched my account to Schwab in May 2020. 1099 data from January to May 2020 is available in PDF only and can not be uploaded directly into Turbo Tax. Found online ways to change PDF to tax file but don't know if they are safe?

Re: How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

wt taxpayer — Mon, 15 Mar 2021 19:48:28 GMT

This is not a simple process. Have to convert the PDF to CVS before it can be converted to a TXF file. The CVS file does not capture all the necessary information. Assistance, including using a paid online service, would help as I don't want to have to type in the 20 some pages of information.

Re: How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

JohnB5677 — Tue, 16 Mar 2021 14:50:52 GMT

There is an alternative.

If there are more than a few transactions you can quickly enter this manually.

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.

Tell us about your 1099-B sales for this account
Answer the questions
Since you have more than a few sales, we recommend entering sales section totals
Continue
Before entering sales section totals, take a moment to find them on your 1099-B
Continue
Now, we'll enter one sales section total on your 1099-B
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.

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

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

Re: How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

fanfare — Tue, 16 Mar 2021 14:56:47 GMT

USAA is a partner with TurboTax and so is Schwab.

you should be able to use the Import from financial institution feature.

Re: How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

wt taxpayer — Tue, 16 Mar 2021 17:35:34 GMT

fanfare Thank you for your input. USAA investments were moved to Schwab on May 26, 2020 and the USAA Investment Management Company was dissolved removing the system and data required for import to Turbo Tax.

Re: How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

wt taxpayer — Wed, 17 Mar 2021 18:19:16 GMT

Did not have to change the PDF. Followed John's advice and Turbo Tax allowed me to upload the PDF and they will send it to the IRS.

Re: How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

wt taxpayer — Fri, 19 Mar 2021 19:56:54 GMT

As noted by John I do have to mail in the 8453 and a copy of the PDF to the IRS.

Re: How can I change a PDF investment 1099 file to a tax file so I can upload to Turbo Tax?

Mark-D — Fri, 16 Feb 2024 23:10:10 GMT

TurboTax should develop code like Generative AI so it can scan a PDF file for a 1099 or W-2 and get the data and put it into TurboTax. There are still so many 1099's out there where one cannot download the data, and I would prefer TurboTax to do the work and then let me verify, instead of me typing in the data where it is easier to make a mistake.

In today's environment "generative artificial intelligence (AI)" per Wikipedia "artificial intelligence capable of generating text [...] or other data using generative models, often in response to prompts. Generative AI models learn the patterns and structure of their input training data and then generate new data that has similar characteristics."