A billing server receives charge data from a card authorization terminal. The charge data indicates a transaction amount, such as a purchase price, and a first financial account, such as a credit card account. The billing server determines a second financial account that corresponds to the first financial account. For example, the second financial account may be the financial account of an insurance company or other reimbursing party. The billing server also determines a reimbursement amount that corresponds to the first financial account. The second financial account is charged the reimbursement amount. Thus, a portion or all of the transaction amount is paid by a reimbursing party. The second financial account is only charged if a reimbursement rule is satisfied. For example, only purchases made at certain types of merchants may be reimbursed. In addition, the billing server may first request approval before charging the second financial account.