A payment processing system for mobile point-of-sale transactions from a mobile point of sale terminal including a payment card reader having a card interface configured to read data from a payment card, the payment processing system includes an automated support system for proactively generating and presenting support messages for merchants using a mobile point-of-sale terminal. The automated support system generates the support message using a current account context for the merchant account and a plurality of rules that indicate a problem with the merchant account. The automated support system is further configured to generate a plurality of rules for detecting merchant account problems using a knowledge database of support tickets that include a human generated response to a merchant account problem and a corresponding merchant account context at the time of the human generated response.