A message manager is capable of analyzing a number of inputs to dynamically adjust rules used to delete messages as well as determine what kinds of messages are likely candidates to be deleted due to their being stale. If a message is determined to be a likely candidate for deletion, the message manager may query the user if they want to delete all messages with similar characteristics, e.g., sender, title, dates sent, time sent, recipients, content, context, and the like. If the user selects “yes” then the message manager may automatically update its deletion rules and further delete all messages in accordance with the user's selection.