Methods and systems for optimizing timing of sending communications to a user device are disclosed. The method includes identifying a first group of user objects having a first attribute. The method includes locating active checkpoints within a user path with each active checkpoint having a user object associated therewith. The method includes forming a second group of the user objects associated with the active checkpoints. The method includes removing, with a processing device, user objects from the first group and the second group that match a second attribute to form a third group with the remaining user objects form the first group and the second group. The method includes processing the active checkpoint for each user object of the third group in response to forming the third group.