Embodiments are provided for generating intelligent account reconfiguration offers to users of a content management system. The content management system may monitor how a user utilizes available features and/or storage space to determine whether the user would be amenable to an offer to reconfigure their user account. Such account reconfiguration offers may include an offer to alter the amount of storage space and/or features available to the user account. The storage space and/or features offered as part of an intelligent account reconfiguration offer may be specific to one particular type of content category, or, for example, may be a function of activity in multiple content categories, based on analysis of historical user data across the entire content management system.