I don't know anything about Goodwill, but the ItsDeductible program cannot handle any single item worth more than $500.
A single item valued at over $500 requires additional information and forms present in the TurboTax product during return preparation.
If you have an item worth more than $500, see the rules on reporting and recordkeeping requirements in this IRS Publication 526--Charitable Contributions:
<a rel="nofollow" target="_blank" href="
https://www.irs.gov/publications/p526#en_US_2017_publink1000229844">https://www.irs.gov/publications...>
