Ali Hopyar ( https://hibernate.atlassian.net/secure/ViewProfile.jspa?accountId=557058%... ) *updated* an issue Hibernate ORM ( https://hibernate.atlassian.net/browse/HHH?atlOrigin=eyJpIjoiZWNlYWQ0MmVk... ) / Bug ( https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiZWNlYW... ) HHH-14079 ( https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiZWNlYW... ) Orphan removal does not work on session.update function ( https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiZWNlYW... ) Change By: Ali Hopyar ( https://hibernate.atlassian.net/secure/ViewProfile.jspa?accountId=557058%... ) Let's say I have two entites like {code:java}@ Entity Table (name = " Parent parent_entity ") @ Table Entity (name = " parent ParentEntity ") public class Parent ParentEntity extends PersistentEntity { @OneToOne(cascade = CascadeType.ALL) @ Transient JoinColumn(name = "inner_entity") private SomePOJO transient 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 = " parent innerEntity ", cascade = CascadeType. All ALL , orphanRemoval = true) private List< Child ChildEntity > children = new ArrayList<>() ; //getters, setters and other fields public List<ChildEntity> getChildren() { return children; } public void setChildren(List<ChildEntity> children) { this.children = children; } } @ Entity Table (name = " Child child_entity ") @ Table Entity (name = " child ChildEntity ") public class Child ChildEntity extends PersistentEntity { @ManyToOne @JoinColumn(name = "inner_entity") private Parent parent InnerEntity innerEntity ; @Column(name = "child_value") //getters, setters and other fields 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 ( 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 )