You should always get a receipt when donating to Goodwill, even when the items appear to be of modest value. The receipt usually includes the charity’s name, the date of contribution, and a general description of the property. You should supplement that receipt with your own detailed list of items and reasonable fair market value estimates. For any single contribution of 250 dollars or more, a contemporaneous written acknowledgment from Goodwill is required, so keeping a receipt is essential. Once your total noncash charitable contributions exceed 500 dollars for the year, you must file Form 8283. Having clear receipts and itemized records will make it far easier to complete the form accurately and to defend your deduction if it is later reviewed by the IRS.