Do I need receipt proof for items I donated to Goodwill under $500 if I dropped off and didn't speak with anyone?
You may not need a receipt from Goodwill for drop-off donations, if the value is $250 or less and you have maintained written records of the donation that includes:
The names of the charity
Date of contribution
A resonably detailed description of the donated property
The fair market value of the property at the time of donation.