In various example embodiments, a system and method for a proactive customer support system are provided. In some example embodiments, outgoing communications from an application server to a client device are monitored for error messages, outgoing error messages are detected, an error type for an error message is determined, an issue ticket including the error message and the error type is generated, and instructions are transmitted that cause a customer service device to display the issue ticket. In some example embodiments, the system additionally assigns a priority score and ranks open error tickets based on their respective error messages. In some example embodiments, the system provides a help message to the client device based on the error message, receives an information request from the client device, determines a reply message based on the information request, and transmits instructions to the client device to display the reply message.