A system and method for proactively sending hosted content items to user computing devices. In one implementation, an online content management system collects access event data representing a plurality of access events pertaining a plurality of hosted content items. The system determines a cross-device access signal for a first hosted content item. The system then detects a first access event pertaining to the first hosted content item. Thereafter, the system determines whether the first access event matches the cross-device access signal. If the first access event matches the cross-device access signal, then the system sends a second hosted content item to a user computing device. The second hosted content item can be the first hosted content item. Alternatively, the second hosted content item can be a content item that is related to the first hosted content item according to the access event data.