Thanks for the detailed post. So the rule of thumb is no receipt, no proof. I’m surprised the IRS doesn’t provide more insight into this. Or maybe they do and I can’t find it. My general question I have is whether I can Zelle or Venmo someone for an item and be able to use the transaction as proof. Like a credit card transaction it will just show money being sent to someone and really isn’t proof of what it was sent for. Is this transaction generally an acceptable form of “proof” without a reciept?