Abstract: Non-limiting examples of the present disclosure describe insight-based routing that is used to improve transparency and communication between customers and support agents of a help desk service. An unresolved case may be identified through a help desk service. Case details associated with the unresolved case may be evaluated. In examples, an evaluation of the case details may comprise analyzing an issue that requires resolution, detecting a case state that corresponds with one or more actions taken to resolve the issue of the unresolved case and detecting, through the help desk service, user presence information indicating availability of a customer associated with the unresolved case. A follow-up inquiry may be generated based on the detected case state. The follow-up inquiry may be automatically transmitted to the customer based on an evaluation of the user presence information indicating that the customer is available.