Retention of events of an ordered event stream is disclosed. Expiration of events stored in a segment of an ordered event stream (OES) can be desirable. New events are added to a head of an OES segment, and pruning events from a tail of the OES segment can be valuable. Processing applications can register a processing scheme for a segment, e.g., at-least-once processing, exactly-once processing, etc., and can generate checkpoints indicating a degree of advancement in processing events of the segment. The ordered event stream can determine a cut point indicative of a progress point, that before which, events of an OES can be marked as ready for expiration. However, events that are marked for expiration can be retained to allow processing based on a checkpoint, e.g., expiration of the event can be refused until there is an assurance the event was read by the processing application.