You should always get a receipt for donation any time you donate items to a charity. Donations made to a single charity on a single day are limited to a value of $500 without an appraisal. You MUST get a receipt. Individual items donate in drop boxes where you cannot receive a donation should be much lower so that you don't draw attention to the fact that you are making large donations without a receipt. I personally make donations to several charities throughout the year and have never had a problem with the IRS.
Using ItsDeductible throughout the year is the easiest way to keep up with your donations. I print out the list of donated items with their estimated value and staple it to the receipt I received from the charity.
