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The reason that you are getting so many instructions is that you have several options for how you enter something like this.  The easiest is to enter the net gain as regular income and call it a day.  Personal item sales are only taxable if they have a gain and then only the gain is taxable.  You properly separated them out and so you can easily enter in the amount that is not subject to income tax.  There is a box at the top of 1040 schedule 1 just for that purpose now.   When you enter the 1099-K into TurboTax you will enter all of the information from the form and then check the box for 'Personal Item Sales'.  Then, on the next screen, you will check the box that says "I sold some items at a loss or had no gain."  In that box you will enter the amount that is excluded from income (in your case $3,237.11) and then it will enter everything into the forms just fine.  Save your records in case there are ever questions and you're done.

@drcox @taxnovice We all seem forced to dance around this counter-intuitive [dare I say nonsensical ?] TurboTax behaviour.  Every other software package is nice enough to the user and helps him/her avoid mistakes. The TurboTax data import behaviour I expect is along the same lines: 1 - have a check box next to each tax form / account seen at my financial institution;  done already 2 - let me check / select or uncheck / clear each box individually;  done already 3 - import ONLY the tax forms I selected;   to be done 4 - IF an imported tax form already exists in my data file, ASK ME FOR PERMISSION to overwrite it; if no permission given, leave it as is;   to be done   Above all, warn me about possible inconsistencies, but TRUST ME to know what I am doing. This would be correct, friendly and logical software behavior.

Aysoref, I greatly appreciate you re-posting this update and all your efforts to resolve this issue with TT.   This is a cop-out by TT, they simply need to change this statement to a question "do you want to over-write your existing import data or add as supplemental data?" as they had in previous years.  It is on the user (as always) to reply to the question as appropriate to their specific needs.  This would support those of us who receive supplemental tax forms every single year.   This year I spent hours editing imported data pertaining to gains/losses on inherited investments.  To not lose this data my only options now are to spend additional hours keying in the minutia of text contained in the new supplemental statement or mail in a copy of my actual supplemental statement to the IRS.  The latter option defeats the whole purpose and security of e-filing.   TT is likely unwilling to change their software for this obvious defect since it is so close to tax deadline.  I am curious if any of the other TT products (I am using the desktop deluxe version) can handle this issue properly this year. I would be willing to upgrade if I knew that it would help resolve the issue.     I sincerely hope that TT reconsiders their position on this topic for next year and modifies their code appropriately, otherwise I will need to look for new tax software after years of being a dedicated TT user.   Again, appreciate your efforts on this.  

In your screenshot, I see the blue hyperlink for the turbotax.exe file; what happens when you just double-click on it, and don't use the Free Download Manager?   Here's how to Contact TurboTax Support for more help.   @Fibrepunk     

Try a Manual Update.  It must be due to some security/connection issue in your particular configuration.  There have been many OS/browser security updates this year.    Try Clicking the icon in front of the URL on a browser window, open the Settings, and choose 'Allow' for the LAN setting.     Here's how to Contact TurboTax Support.   @mcneff12     

The same problem exists in the Massachusetts 2024 Turbo Tax program.  I went back through prior year programs and found prior to 2023 the prior year Capital losses transferred properly into the subsequent year. I also found that the losses generated in 2024 did not transfer into Turbo Tax Delux 2025. That is a MAJOR FLAW and needs to be addressed immediately!  

Sadly it won't do any good to rant to TT about a "poor" decision they made nor to mention other things that bother you. I looked for other viable options and after checking several I filed my returns using FreeTaxUSA. Their program did everything I needed to do and I will most likely use them for my 2026 returns. Customer service answered questions very timely and the best part was the fee was considerably less than TT or any of the others.

Windows 10 was supported for another year but I guess that didn't affect TT's decision to not support it. How did that affect my using TT this year? I walked away from TT and used another tax software program.