The present invention discloses a solution for tracking email dispersion through content substitution. In the solution, a set of entities to receive an email can be identified, where the email can contains textual content. A subset of words contained within the textual content can be programmatically selected. A set of replacement words for each of the determined words can be determined. For each email receiving entity, at least one replacement word can be programmatically substituted for it's equivalent to generate an entity specific message. Each entity specific message can contain a unique combination of substitutions so that no two entity specific message are identical. A record of which email receiving entities are associated with which entity specific message can be maintained. The entity specific messages can be sent to the associated set of email receiving entities.