Abstract: An example system and method for monitoring digital conversations is described. In particular, conversations are monitored for periods of inactivity, where upon identifying a particular period of inactivity, further communications are automatically generated to refresh and restart the conversations based on one or more predefined messages. In one example method, a communication target is identified, where the communication target is associated with an existing conversation. An inactivity-based rule is associated with the target and the conversation, the rule associated with an inactivity time and at least one message. Activity associated with the conversation is monitored to determine whether a time of inactivity exceeds the inactivity time. In response to determining that the inactivity time exceeds the inactivity-based rule, a new message is automatically generated and transmitted to the target based on the at least one message of the inactivity-based rule.