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beckie-d
New Member

Cant upload my gains report from CryptoTaxCalculator keeps saying "We're having trouble with your file"

Have tried uploading it multiple times in the last few days and it keeps telling me the same thing "We’re having trouble with your file"
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5 Replies
DavidD66
Expert Alumni

Cant upload my gains report from CryptoTaxCalculator keeps saying "We're having trouble with your file"

I can't help if the download of your crypto report isn't working properly; however, there is an alternative.  You can enter your category totals instead of individual transactions.  To do so in TurboTax Online:

 

  • Make sure you are logged in and working in your return
  • Click on the Search Icon  (magnifying glass)
  • In the Search Window type 1099-B
  • Click on "Jump to 1099-b"
  • Click Add investment (if the account you were trying to download is showing, delete it first)
  • On the Let's import your tax info screen, click on Enter a different way at the bottom right of the page
  • On the page with "OK, let's start with one investment type" click on "Stocks, Bonds, Mutual Funds" and then Continue
  • Enter your information for your crypto broker
  • On the page with "Tell us about your 1099-B sales for this brokerage account" answer the question about employee stock & the number of sales, etc.
  • On the screen with Now, choose how to enter your sales click the button "Sales section totals" and click on Continue
  • Enter your Investment Sales Section Totals and repeat till you have entered for each category.

After entering all your sales section totals,  Look for "Now we'll help you upload your 1099-B since the IRS requires a copy" and follow the instructions,  or you can mail a paper copy of your 1099-B to the IRS.  If you want to mail, click on "How do I mail my statement".

 

Take a moment to double-check that your statements are complete. For each sale listed, there should be:

  •  - A Description
  •  - Date Acquired
  •  - Date Sold
  •  - Sales Price
  •  - Cost Basis
  •  - Gain or loss for each sale
  •  - A based on how the sale was reported to you and the IRS

 In some uncommon cases, there will be an adjustment code and adjustment amount.

 

 Here's how to mail your statements:

 

 If you are e-filing your tax return, then mail your statements along with Form 8453 to:

 

Internal Revenue Service

Attn: Shipping and Receiving, 0254

Receipt and Control Branch

Austin, TX 73344-0254

 

If you are not e-filing, then mail your statements with your entire tax return to your local IRS office.

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beckie-d
New Member

Cant upload my gains report from CryptoTaxCalculator keeps saying "We're having trouble with your file"

i appreciate your reply but this has to do with crypto not stocks, it should be able to be uploaded straight from computer i dont understand why this is all of sudden an issue.

JamesG1
Expert Alumni

Cant upload my gains report from CryptoTaxCalculator keeps saying "We're having trouble with your file"

One option for reporting crypto transactions is to report summary information from an IRS form 8949 or IRS form 1099-B.  Some crypto services generate an IRS form 8949 which may be reported following the steps outlined by @DavidD66.  It may seem confusing when on the page "OK, let's start with one investment type", you are asked to click on "Stocks, Bonds, Mutual Funds" with no mention of cryptocurrency.

 

Are you attempting to import your information at the screen Let's import your tax info?

 

Or are you trying to upload a .CSV file at the screen OK, let's start with one investment type?

 

Or are you attempting another option?

 

@beckie-d 

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beckie-d
New Member

Cant upload my gains report from CryptoTaxCalculator keeps saying "We're having trouble with your file"

this is the error its giving me Screenshot 2025-02-28 164532.png

 

VictoriaD75
Employee Tax Expert

Cant upload my gains report from CryptoTaxCalculator keeps saying "We're having trouble with your file"

Please see the following thread with some possible solutions to your upload error:

 

Cryptocurrency upload problems

 

@beckie-d 

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