I am having a very similar problem with Form 8283 with my return. I made 6 donations of household goods to 5 charities in 2025. One charity received two donations on two separate days, all household goods. On one day, the fair market value was > $500. The second donation was not. The remaining donations to the other 5 charities were all < $500. TurboTax is only populating the one donation that was greater than $500 on 8283. It's my understanding that ALL items to ALL 5 charities need to populated on Form 8283 since I have over $500 total in item donations this year. For reference, FreeTaxUSA (as a comparison) is correctly populating Form 8283 with all 6 donations to all 5 charities.
For troubleshooting, I deleted all item donations in TurboTax and re-entered them manually. The first two charities were < $500. When I got to the > $500 charity, I was prompted to enter the address and fill out the cost basis information. When I went back to my donation list, the first two charities now were flagged as needing review. I went back in and was prompted to enter their address (which is correct since that's needed for Form 8283). However, they still don't show on the form.
Aside from doing a manual override (which generates dozens of errors for every field), I'm not sure how to fix this and believe it to be a bug.
