Ali Hopyar ( https://hibernate.atlassian.net/secure/ViewProfile.jspa?accountId=557058%... ) *updated* an issue Hibernate ORM ( https://hibernate.atlassian.net/browse/HHH?atlOrigin=eyJpIjoiYmJmYzM1Yjgz... ) / Bug ( https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiYmJmYz... ) HHH-14079 ( https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiYmJmYz... ) Orphan removal does not work on session.update function ( https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiYmJmYz... ) Change By: Ali Hopyar ( https://hibernate.atlassian.net/secure/ViewProfile.jspa?accountId=557058%... ) Let's say I have two entites like {code:java}@Table(name = "parent_entity") @Entity(name = "ParentEntity") public class ParentEntity extends PersistentEntity { @OneToOne(cascade = CascadeType.ALL) @JoinColumn(name = "inner_entity") private InnerEntity innerEntity = new InnerEntity(); public InnerEntity getInnerEntity() { return innerEntity; } public void setInnerEntity(InnerEntity innerEntity) { this.innerEntity = innerEntity; } } @Table(name = "inner_entity") @Entity(name = "InnerEntity") public class InnerEntity extends PersistentEntity { @OneToMany(mappedBy = "innerEntity", cascade = CascadeType.ALL, orphanRemoval = true) private List<ChildEntity> children = new ArrayList<>(); public List<ChildEntity> getChildren() { return children; } public void setChildren(List<ChildEntity> children) { this.children = children; } } @Table(name = "child_entity") @Entity(name = "ChildEntity") public class ChildEntity extends PersistentEntity { @ManyToOne @JoinColumn(name = "inner_entity") private InnerEntity innerEntity; @Column(name = "child_value") private String childValue; public InnerEntity getInnerEntity() { return innerEntity; } public void setInnerEntity(InnerEntity innerEntity) { this.innerEntity = innerEntity; } public String getChildValue() { return childValue; } public void setChildValue(String childValue) { this.childValue = childValue; } } {code} When I call session.update with parent entity, orphanRemoval does not have any affect. It does not delete child entity and relationship between parent and child. I have tried with 5.3.7.Final, 5.4.15.Final, 5.4.16.Final and 5.4.17 Final Test Case can be found in attachment ( https://hibernate.atlassian.net/browse/HHH-14079#add-comment?atlOrigin=ey... ) Add Comment ( https://hibernate.atlassian.net/browse/HHH-14079#add-comment?atlOrigin=ey... ) Get Jira notifications on your phone! Download the Jira Cloud app for Android ( https://play.google.com/store/apps/details?id=com.atlassian.android.jira.... ) or iOS ( https://itunes.apple.com/app/apple-store/id1006972087?pt=696495&ct=Em... ) This message was sent by Atlassian Jira (v1001.0.0-SNAPSHOT#100130- sha1:10d2092 )