Do I really have to just lie to the IRS to get TurboTax to accept short sale dates?

[dandy48]

I have traded many stock options. They all were opened with a short sale followed by covering the short position. The 1099-B has all the correct dates and they were transferred correctly to TurboTax but TurboTax says all the dates are in error because the sale date is before the purchase date. This means a lot of work manually entering every trade with incorrect dates just to be able to use TurboTax.

[GeorgeM777]

Given the large number of transactions you have, one option to get around the error message is to report a summary of your gains/losses on Schedule D Capital Gains and Losses versus listing each one on Form 8949 Sales and Other Dispositions of Capital Assets.  However, to report a summary on Schedule D, the basis for your option trades must have been reported to the IRS.  Namely, the option trades must be covered trades (Box A or Box D). 

@dandy48

[dandy48]

I already spent a couple of hours swapping all the dates. This is what I had to do with TurboTax last year.  I was hoping the software had some other way because it makes using TurboTax not really worth the effort.

For future reference how would TurboTax allow me to import the data so that I had the other information (dividend/interest, etc.) from the brokerage, but then delete all the individual trades and manually enter just totals on Sch D? 

[GeorgeM777 · Accepted solution]

You could import your 1099-B, then delete Form 8949.   Here are the steps to delete a form using TurboTax online.

1. Open or continue your return in TurboTax.
2. In the left menu, select Tax Tools and then Tools.
3. In the pop-up window Tool Center, choose Delete a form.
4. Select Delete next to the form/schedule/worksheet in the list and follow the instructions.

To report just a summary of your transactions, follow these steps:

1. Go to Income & Expenses,
2. scroll down the page to Investment Income,
3. select Stocks, Cryptocurrency...
4. at the page where you can import your transactions, select I'll type it myself,
5. on the page Now, choose how to enter your sales, select Sales section totals,
6. enter your information when prompted.

@dandy48