Non-limiting examples describe automated management of rich content previews associated with bundled content of an application/service. As an example, a bundle of content may be a bundle of emails created within an email service. Email content associated with a bundle of emails may be accessed. The email content may be evaluated based on application of machine learning model that: determines an entity type associated with the bundle of emails based on the tag, identifies a state associated with the bundle of emails, and determines relevancy of specific email content in association with a determined entity type and the identified state associated with the bundle of emails. A rich content preview for the bundle of emails may be generated based on an evaluation of the email content.