Imagine finally getting around to donating all the junk you had lying around, only to be denied the deduction when you try to claim it. Believe it or not, this really happened, and it now serves as a wake-up call to all who make charitable donations as a part of their tax strategy and legacy planning.

Here’s what you need to know to ensure this doesn’t happen to you.

The Implications of Improper Documentation

In Besaw v. Commissioner, decided on July 21, 2025, John Besaw donated $6,760 worth of goods to charity and, despite legitimately donating every reported item, was denied his entire deduction. The court noted that “none of the receipts described the items”; therefore, failing to comply due to his lack of proper documentation. 

The court can be cruel and unforgiving when it comes to the rules on charitable documentation. There were two main reasons why Besaw’s deduction was denied:

• Missing Dates: He did not record specific donation dates for the donated items on his 8283 tax form filed with his return.
• Missing Values: He left the fair market value column blank on his 8283 tax form.

When the IRS questioned the deduction, Besaw tried to edit the donation records, but was unsuccessful. He was too late; once an audit begins, you can not alter it.

How to Document Your Next Donation

To avoid making the same mistake as Besaw, you should have everything complete and filled out before you leave your house. Here is a checklist to ensure you stay compliant:

Property Cost	Requiered Documentation
Over $250	A “contemporaneous written acknowledgment”, dated earlier than the date you file or the return’s due date (including extensions).
Over $500	Records showing how and when you acquired the property, its original cost, and its adjusted basis.
Over $5,000	A qualified appraisal is needed for most property types.

Contemporaneous is an important concept to understand. All tax authorities expect due diligence (e.g. records) to be satisfied close to the event instead of a long period of time after the fact.

Compliance Checklist:

• Make a list of every item with its:
  • Description
  • Acquisition date
  • Original cost
  • Fair market value

• Take photos of all your items before donating them.
• Give the charity your list when you donate your items and ask the attendant to reference or incorporate your list into their official acknowledgment receipt.
• Before you file your return or by the return’s due date (including extensions), make sure to have the official acknowledgment form.

Why This Matters

When making charitable donations, documentation is crucial to compliance. The IRS is strict with the rules on charitable giving and demands that you follow them exactly. Something as small as missing a single donation date is enough to void your entire deduction.

If you are looking to optimize your tax strategy and avoid penalties, contact a certified CPA today.

Resources

IRS Publication 526: Charitable Contributions

Instructions for IRS Form 8283 (Noncash Charitable Contributions)

IRS Publication 561 (PDF)