How to delete entities in a chained one-to-many and many-to-many JPA relationship - jpa

Question

I have a chain of entities as follows:
#Entity
#Table(name = "Patients")
public class Patient extends TimeStampedPersistable{
private static final long serialVersionUID = 1L;
#OneToMany(mappedBy="patient", cascade = CascadeType.ALL)
#PrivateOwned
private List<Insurance> insurances;
}
#Entity
#Table(name = "insurance")
public class Insurance extends PersistableEntity {
private static final long serialVersionUID = 1L;
#ManyToOne(optional=false)
#JoinColumn(name="patient_id", nullable=false)
private Patient patient;
#Column(name = "policy_number", unique = false, nullable = true)
private String policyNumber;
#ManyToMany(fetch = FetchType.LAZY, cascade = CascadeType.PERSIST)
#JoinTable(name = "insurance_companycodes", joinColumns = {
#JoinColumn(name = "insurance_id", referencedColumnName = "id", nullable = false, updatable = false) }, inverseJoinColumns = {
#JoinColumn(name = "insuranceCompanyCode_id", referencedColumnName = "id", nullable = false, updatable = false) })
private Set<InsuranceCompanyCode> insuranceCompanyCodes = new HashSet<>();
}
#Entity
#Table(name = "insurance_company_codes")
public class InsuranceCompanyCode extends PersistableEntity {
private static final long serialVersionUID = 1L;
#Column(name = "identifier", unique = true, nullable = true)
private String identifier;
#ManyToMany(mappedBy = "insuranceCompanyCodes", fetch = FetchType.LAZY)
private Set<Insurance> insurances = new HashSet<>();
}
I need to remove insurance items from the Patient object. I am using the following code:
for (Iterator<Insurance> iterator = patient.getInsurances().iterator(); iterator.hasNext();) {
iterator.next();
iterator.remove();
}
This seems to work for child entities that don't have child entities, however in this situation the Insurance entity has child entities and is not actually removed (no exceptions are displayed). Note, I am using the EclipseLink specific annotation #PrivateOwned which I expected would have forced the removal of the Insurance entities.
Any guidance, suggestions appreciated!