Hi James,
Thank you for responding. See a few questions in the below while reviewing
In summary, when entering a 1099‑K for a profit, the question “Enter the total proceeds for items sold at a loss” should be left blank. Click Continue, then go to:
Investment Income → Stocks, Crypto, Mutual Funds, Bonds, Other → Personal Items
From there, enter the remaining details. TurboTax will correctly report the gain, generate Schedule D, and NOT populate the line that reads, “For 2025, enter the amount reported to you on Form 1099‑K that was included for personal items sold at a loss.” That seems appropriate since the transaction resulted in a gain rather than a loss, but I’d appreciate confirmation that this is the intended behavior.
Given this workflow, should TurboTax consider improving the wording on the “sold at a loss or had no gain” section? Perhaps adding guidance such as “If you had a gain, leave this blank,” or even including a third radio button for users who had a gain. In my modest opinion, TurboTax may assume most personal item sales result in a loss, which could explain why the current language only addresses losses and not profits.
Possibly something to consider for future versions. I’d be interested in your thoughts.
