Techniques for rules-based workflow messaging are described herein. In one or more implementations, user activity with different existing workflows for features of an application is tracked and communicated to a tracking service. Based on analysis of user activity, rules are derived regarding messages to show users with respect to new features that relate to user interaction. For example, activity data indicating heavy usage of a particular legacy workflow is used to recognize that users are not discovering/using a corresponding new feature. Based on such usage patterns, workflow messages and rules for exposing the messages for the new feature are created and distributed to clients. The rules are applied to detect workflow patterns and trigger messages regarding corresponding new features. In response to an indication of interest in a new feature, interactive instructions to guide users step-by-step through the workflow for a new feature are provided.