JPA: Cascade remove does not delete child

Question

Edit: Modifying the question to better reflect the problem. Originally posted question here

I have a parent (Context) and a child (User) en

Answer 1

Don't map your relation table as en entity. Use @ManyToMany Instead and make your user entity owner of the relationship.

Edit :

So your association table primary key must be composed of both foreign key.

See this http://giannigar.wordpress.com/2009/09/04/mapping-a-many-to-many-join-table-with-extra-column-using-jpa/