+++ This bug was initially created as a clone of Bug #1182303 +++ Description of problem: @Entity public class Product { @Id @GeneratedValue(strategy=GenerationType.AUTO) private Long id; @OneToMany(mappedBy = "product", orphanRemoval = true) private List<Feature> features = new ArrayList<Feature>(); ... } @Entity public class Feature { @Id @GeneratedValue(strategy=GenerationType.AUTO) private Long id; @ManyToOne() private Product product; ... } This affects EntityManager only. https://hibernate.atlassian.net/browse/HHH-9330 How reproducible: easy to reproduce. Steps to Reproduce: See the tests in org.hibernate.ejb.test.orphan.onetomany.DeleteOneToManyOrphansTest for details. Actual results: Clearing the collection of features in the Product will not result in deleting all Features of that product. Expected results: Features that were cleared should be deleted. Additional info: The workaround is setting the CascadeType.PERSIST in the Product entity. Tests (which work properly) for Hibernate core are in org.hibernate.test.orphan.onetomany.DeleteOneToManyOrphansTest. --- Additional comment from Gail Badner on 2015-01-14 21:55:56 CET --- This was fixed in 4.2.17.Final.