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In many cases, if you don't have records of a particular business expense, but it's obvious that you must have incurred it, in an audit situation the IRS will estimate the amount of your expenses and allow you to deduct them. An example would be a retailer who has incomplete records of inventory purchases the IRS will come up with a reasonable estimate of what the purchases should have been.
However, certain types of expenses, which the IRS has found to be particularly susceptible to cheating, are subject to special documentation rules. The following expenses must generally be proven by adequate records or other evidence; if you have no records, the deduction will be completely disallowed:
For meals, entertainment, business gifts and computers, you must keep receipts for any expense that is at least $75. You must have a receipt for all lodging expenses whatever the amount. For transportation expenses, a receipt is not needed if it is not readily available.
You must also substantiate each individual expense as to:
For entertainment and gift expenses, you must also note the business relationship of the person(s) being entertained or receiving a gift.
These things can be noted on the back of the receipt, or recorded in a formal expense log. For vehicle expenses, you'll also have to keep a mileage log.