As I taught my tax course students ... look at the situation from the IRS auditor's perspective. If you say you paid your dentist $1000 and it shows that on a CC statement as a payment to Dr. X DDS then could the auditor agree that the money was paid for only dental work ? I would say yes but if you went to Walgreens or Walmart for your prescriptions and all you had was the CC statement then it could easily be denied since you can buy a lot from those places that are not deductible prescriptions.
I have the same issue with my bookkeeping clients ... I only get their bank/CC statements and not the actual reciepts so they have to guess/determine what they bought at say WAWA... (I do ask for the recipts if the clients cannot tell me what it was for exactly ... of course I get to know the buying habits of my clients and request they don't use the business CC for personal expenses and some actually comply when I stress the negatives of being audited). If they paid $60 then it probably was gas for the car/truck or $15 fuel for the mowers but $.99 was probably a fountain drink. The auditor will want substantiation of the expenses if audited and the CC/bank statements will probably not be enough and it is on the taxpayer to provide the proof.
