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Should I import my data from TD Ameritrade as Gainskeeper or the standard TD Ameritrade 1099?

  • I have a bunch of WASH Sales as part of my trading.  Also, I have net loss this year.
It is easiest to import gain/loss info (1099-B) from Gainskeeper, because Gainskeeper tracks your basis, even for older "non-covered" holdings. Import your other income (1099-INT, 1099-DIV, and 1099-MISC) info from TD Ameritrade.

Ameritrade has some videos which may help with this. What I said above is what they recommend. Unfortunately, that seems to be their only online help (i.e., no written instructions that I could find). There is also a video about wash sales you ought to see.
  • I found some textual help on the TDA web site:

    TurboTax (installed version)

    TurboTax uses TD Ameritrade to import dividend and interest information, and GainsKeeper® for buy/sell information. You must manually enter 1256 contract data. Wash sales will be calculated.

    Import from TD Ameritrade

        Open TurboTax and display your tax return.
        Click the File menu at the top left.
        Point to Import, then From Financial Institution.
        Type "TD" below I'm Looking For, click TD Ameritrade in the lower window to highlight, and then click Continue.
        Type your 9-digit account number and your 10-digit Document ID, and click Continue.
        Remove the checkmark to the left of TD Ameritrade – 1099-B, if listed. Click each remaining checkbox to place a check to the left of each item listed, and click Import Now.
        Click the blue Done button at the bottom right of the Import Summary screen.

    Import from GainsKeeper

        Open TurboTax and display your tax return.
        Click the File menu at the top left, point to Import, and click From Financial Institution.
        Type "gai" in the box below I'm looking for, click GainsKeeper to highlight in blue, and then click the blue Continue button towards the bottom right.
        Type [your 9-digit account number]@amtd (with no spaces) for the UserID and your 4-digit PIN for the Password and click Continue.
        Place a checkmark to the left of 1099-B, and click Import Now.
        Review the details prior to accepting the data available for import. If you need to manually enter additional cost basis information, do so now.
        Click Done at the lower right of the Import Summary page to proceed.

    Section 1256 contract data is not included in the import from TD Ameritrade.

    If you have any 1256 contracts to report:

        Open TurboTax and display your tax return.
        Click the Federal Taxes tab at the top middle and click Wages & Income to the left side to manually enter your 1256 contract data.
        Click Explore on My Own in the middle of the page.
        Click the Start button to the right of the Contracts and Straddles item in the Investment Income section.

    TurboTax (online version)

    Turbo Tax uses TD Ameritrade to import dividend and interest information, and GainsKeeper for buy/sell information. You must manually enter 1256 contract data. Wash sales will be calculated.

    Import from TD Ameritrade

        Log in to your online TurboTax account and display your return.
        Click the gray Federal Taxes link at the left sidebar, click Wages & Income, and then click Explore on My Own at the middle right of the page.
        Click the blue View button to the right side of the Import Summary section. Click the Add Other Documents button on the left side within the Import Summary section.
        Type "TD" under Import from my bank or brokerage, click to highlight TD Ameritrade in blue, and click the blue Continue button to the bottom right.
        Type your 9-digit account number and your 10-digit Document ID and click Continue.
        Remove the checkmark to the left of TD Ameritrade – 1099-B, if listed. Each remaining item listed needs to be checked. Click the blue Import Now button towards the bottom right.
        Click the blue Done button at the bottom right of the Import Summary screen.

    Import from GainsKeeper

        Log in to your online TurboTax account and display your return.
        Click the gray Federal Taxes link at the left sidebar, click Wages & Income, and then click Explore on My Own at the middle right of the page.
        Click the blue View button to the right of the Import Summary section. Click Add Other Documents on the right side within the Import Summary section.
        Type "gai" in the box below Import from my bank or brokerage, click GainsKeeper to highlight in blue, and then click the blue Continue button towards the bottom right.
        Type [your 9-digit account number]@amtd (with no spaces) for the UserID and [your 4-digit PIN] for the Password and click Continue.
        Place a checkmark to the left of 1099-B, and click Import Now.
        Review the details prior to accepting the data available for import. If you need to manually enter additional cost basis information, do so now.
        Click Done at the lower right of the Import Summary page to proceed.

    Section 1256 contract data is not included in the import from TD Ameritrade.

    If you have any 1256 contracts to report:

        Log in to your online TurboTax account and display your return.
        Click the gray Federal Taxes link at the left sidebar, and click Wages & Income.
        Click Explore on My Own at the middle right of the page.
        Click Start to the right of the Contracts and Straddles item in the Investment Income section.

    Instructions pertain to the current tax year. Steps for preparing your return for a previous year differ.
You need to be aware that just importing the 1099-B data into TurboTax does not necessarily fulfill the reporting requirements. The data that are imported by TurbiTax are just the 1099-B data, and they do not include transaction that are not yet required to be reported by the broker to the IRS. These include, among others, 1256 contracts and straddles and options transactions. Importing from GainsKeeper gives better coverage of both cost basis and transactions not included on the 1099-B.

You can import from TDA using the standard import process and the wash sales will be handled correctly. However, if you have transactions of type "box c", transactions not reported on form 1099-B, these will not be imported using the usual method, and you will end up having to enter them yourself. Check your GainsKeeper data to see if you have these kind of transactions. They would be mostly options that expired or were covered. If you have these kind of transactions, it will save you trouble if you create the TXF file from the GainsKeeper data (including wash sales) and import the data from that file, which would include the "Box C" information. I cannot vouch for the fact that the data will all end up classified correctly on the Forms 8949 because I did it the other way, but I suspect that it will work just fine.
  • Using TTBusiness, there is no menu item down from file for "import.." that lists anything but Quickbooks, which I do not use.  However, I have multiple hundreds of 1256 contracts which I need to import.  Need help
  • TT Biz can't help you with this. If you are within your return period, perhaps you'd be better off returning it and hiring a tax pro to enter all those transactions.
  • What can a Tax pro do with this that I can't?  That's is why I bought TTax Business, and TTPremier.  Are you not able to facilitate my situation?  There must be others in my situation!   Is there no TT software to accommodate my situation?
  • We're just users like you and can't help you further. TT Biz does not import from brokerages. I am going to close this thread now because you have hijacked it from its original topic. I suggest you contact TurboTax Support directly if you find the product unusable.