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Delete entries from collection of objects using stateless session in hibernate

Is it possible? I try to do it this way, but it doesn't work:

StatelessSession sess = getSessionFactory().openStatelessSession();
sess.beginTransaction();
MessageDetails md = (MessageDetails) sess.get(MessageDetails.class,1189469L);
md.setCc(null);
sess.update(md);
sess.getTransaction().commit();
sess.close();

cc is defined this way:

@ManyToMany(fetch = FetchType.LAZY, cascade = CascadeType.ALL)
@JoinTable(name = "MessageEntryCc")
public Set<EmailAndName> getCc() {
    return cc;
}

After running code, MessageEntryCc still contains entries with message_details_id = 1189469...

Please add CascadeType=DELETE_ORPHAN as well in your mapping as:

  @ManyToMany(fetch = FetchType.LAZY, 
                      cascade={CascadeType.ALL, CascadeType.DELETE_ORPHAN})

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