diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/collection/ElementCollectionUpdateTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/collection/ElementCollectionUpdateTest.java
new file mode 100644
index 0000000000..bc34d469bf
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/collection/ElementCollectionUpdateTest.java
@@ -0,0 +1,124 @@
+package org.hibernate.orm.test.collection;
+
+import java.util.Arrays;
+import java.util.Collection;
+import java.util.HashSet;
+import java.util.Set;
+
+import org.hibernate.testing.TestForIssue;
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.ElementCollection;
+import jakarta.persistence.Entity;
+import jakarta.persistence.FetchType;
+import jakarta.persistence.Id;
+import jakarta.persistence.Table;
+import org.assertj.core.api.Assertions;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+@DomainModel(annotatedClasses = ElementCollectionUpdateTest.Person.class)
+@SessionFactory
+@TestForIssue(jiraKey = "HHH-16297")
+public class ElementCollectionUpdateTest {
+
+	private Person thePerson;
+
+	@BeforeAll
+	public void prepare(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			Set<String> phones = new HashSet<>( Arrays.asList( "999-999-9999", "111-111-1111", "123-456-7890" ) );
+			thePerson = new Person( 7242000, "Claude", phones );
+			session.persist( thePerson );
+		} );
+	}
+
+	@Test
+	public void removeElementAndAddNewOne(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			Person foundPerson = session.find( Person.class, thePerson.getId() );
+			Assertions.assertThat( foundPerson ).isNotNull();
+			Set<String> phones = foundPerson.getPhones();
+			phones.remove( "111-111-1111" );
+			phones.add( "000" );
+			assertThat( phones )
+					.containsExactlyInAnyOrder( "999-999-9999", "123-456-7890", "000" );
+		} );
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, thePerson.getId() );
+			assertThat( person.getPhones() )
+					.containsExactlyInAnyOrder( "999-999-9999", "123-456-7890", "000" );
+		} );
+
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, thePerson.getId() );
+			person.getPhones().remove( "123-456-7890" );
+		} );
+
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, thePerson.getId() );
+			Set<String> phones = person.getPhones();
+			assertThat( phones )
+					.containsExactlyInAnyOrder( "999-999-9999", "000" );
+			phones.add( "111-111-1111" );
+
+		} );
+
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, thePerson.getId() );
+			Set<String> phones = person.getPhones();
+			assertThat( phones )
+					.containsExactlyInAnyOrder( "999-999-9999", "000", "111-111-1111" );
+
+		} );
+	}
+
+	@Entity(name = "Person")
+	@Table(name = "Person")
+	static class Person {
+		@Id
+		private Integer id;
+		private String name;
+
+		@ElementCollection(fetch = FetchType.EAGER)
+		private Set<String> phones;
+
+		public Person() {
+		}
+
+		public Person(Integer id, String name, Collection<String> phones) {
+			this.id = id;
+			this.name = name;
+			this.phones = new HashSet<>( phones );
+		}
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+
+		public void setPhones(Set<String> phones) {
+			this.phones = phones;
+		}
+
+		public Set<String> getPhones() {
+			return phones;
+		}
+
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/collection/OneToManyUpdateTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/collection/OneToManyUpdateTest.java
new file mode 100644
index 0000000000..7c21f158ff
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/collection/OneToManyUpdateTest.java
@@ -0,0 +1,175 @@
+package org.hibernate.orm.test.collection;
+
+import java.util.Arrays;
+import java.util.Collection;
+import java.util.HashSet;
+import java.util.Objects;
+import java.util.Set;
+
+import org.hibernate.testing.TestForIssue;
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.Entity;
+import jakarta.persistence.FetchType;
+import jakarta.persistence.Id;
+import jakarta.persistence.OneToMany;
+import jakarta.persistence.Table;
+import org.assertj.core.api.Assertions;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+@DomainModel(
+		annotatedClasses = {
+				OneToManyUpdateTest.Person.class,
+				OneToManyUpdateTest.Address.class
+		}
+)
+@SessionFactory
+@TestForIssue(jiraKey = "HHH-16297")
+public class OneToManyUpdateTest {
+
+	private static final Integer PERSON_ID = 7242000;
+
+	@BeforeAll
+	public void prepare(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			Address address1 = new Address( 1, "via milano", "Roma" );
+			Address address2 = new Address( 2, "via Cartesio", "Milano" );
+			Set<Address> addresses = new HashSet<>( Arrays.asList(
+					address1,
+					address2
+			) );
+			Person person = new Person( PERSON_ID, "Claude", addresses );
+			session.persist( address1 );
+			session.persist( address2 );
+			session.persist( person );
+		} );
+	}
+
+	@Test
+	public void removeElementAndAddNewOne(SessionFactoryScope scope) {
+		Address address3 = new Address( 3, "via Pierce", "Milano" );
+		Address address2 = new Address( 2, "via Cartesio", "Milano" );
+		scope.inTransaction( session -> {
+			Person foundPerson = session.find( Person.class, PERSON_ID );
+			Assertions.assertThat( foundPerson ).isNotNull();
+			Set<Address> addresses = foundPerson.getAddresses();
+			Address address1 = new Address( 1, "via milano", "Roma" );
+			addresses.remove( address1 );
+			addresses.add( address3 );
+			session.persist( address3 );
+			assertThat( addresses )
+					.containsExactlyInAnyOrder(
+							address3,
+							address2
+					);
+		} );
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, PERSON_ID );
+			Set<Address> addresses = person.getAddresses();
+			assertThat( addresses )
+					.containsExactlyInAnyOrder(
+							address3,
+							address2
+					);
+			addresses.remove( address2 );
+
+		} );
+
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, PERSON_ID );
+			Set<Address> addresses = person.getAddresses();
+			assertThat( addresses )
+					.containsExactlyInAnyOrder(
+							address3
+					);
+		} );
+	}
+
+	@Entity(name = "Person")
+	@Table(name = "Person")
+	static class Person {
+		@Id
+		private Integer id;
+		private String name;
+
+		@OneToMany(fetch = FetchType.EAGER)
+		private Set<Address> addresses;
+
+		public Person() {
+		}
+
+		public Person(Integer id, String name, Collection<Address> addresses) {
+			this.id = id;
+			this.name = name;
+			this.addresses = new HashSet<>( addresses );
+		}
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+
+		public Set<Address> getAddresses() {
+			return addresses;
+		}
+
+		public void setAddresses(Set<Address> addresses) {
+			this.addresses = addresses;
+		}
+
+	}
+
+	@Entity(name = "Address")
+	@Table(name = "ADDRESS_TABLE")
+	public static class Address {
+
+		@Id
+		private Integer id;
+
+		private String street;
+
+		private String city;
+
+		public Address() {
+		}
+
+		public Address(Integer id, String street, String city) {
+			this.id = id;
+			this.street = street;
+			this.city = city;
+		}
+
+		@Override
+		public boolean equals(Object o) {
+			if ( this == o ) {
+				return true;
+			}
+			if ( o == null || getClass() != o.getClass() ) {
+				return false;
+			}
+			Address address = (Address) o;
+			return Objects.equals( street, address.street ) && Objects.equals( city, address.city );
+		}
+
+		@Override
+		public int hashCode() {
+			return Objects.hash( street, city );
+		}
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/embeddable/EmbeddableAsElementCollectionUpdateTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/embeddable/EmbeddableAsElementCollectionUpdateTest.java
new file mode 100644
index 0000000000..e999ed76cc
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/embeddable/EmbeddableAsElementCollectionUpdateTest.java
@@ -0,0 +1,158 @@
+package org.hibernate.orm.test.embeddable;
+
+import java.util.Arrays;
+import java.util.Collection;
+import java.util.HashSet;
+import java.util.Objects;
+import java.util.Set;
+
+import org.hibernate.testing.TestForIssue;
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.Basic;
+import jakarta.persistence.ElementCollection;
+import jakarta.persistence.Embeddable;
+import jakarta.persistence.Entity;
+import jakarta.persistence.FetchType;
+import jakarta.persistence.Id;
+import jakarta.persistence.Table;
+import org.assertj.core.api.Assertions;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+@DomainModel(annotatedClasses = EmbeddableAsElementCollectionUpdateTest.Person.class)
+@SessionFactory
+@TestForIssue(jiraKey = "HHH-16297")
+public class EmbeddableAsElementCollectionUpdateTest {
+
+	private Person thePerson;
+
+	@BeforeAll
+	public void prepare(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			Set<Address> addresses = new HashSet<>( Arrays.asList(
+					new Address( "via milano", "Roma" ),
+					new Address( "via Cartesio", "Milano" )
+			) );
+			thePerson = new Person( 7242000, "Claude", addresses );
+			session.persist( thePerson );
+		} );
+	}
+
+	@Test
+	public void removeElementAndAddNewOne(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			Person foundPerson = session.find( Person.class, thePerson.getId() );
+			Assertions.assertThat( foundPerson ).isNotNull();
+			Set<Address> addresses = foundPerson.getAddresses();
+			addresses.remove( new Address( "via milano", "Roma" ) );
+			addresses.add( new Address( "via Pierce", null ) );
+			assertThat( addresses )
+					.containsExactlyInAnyOrder(
+							new Address( "via Pierce", null ),
+							new Address( "via Cartesio", "Milano" )
+					);
+		} );
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, thePerson.getId() );
+			Set<Address> addresses = person.getAddresses();
+			assertThat( addresses )
+					.containsExactlyInAnyOrder(
+							new Address( "via Pierce", null ),
+							new Address( "via Cartesio", "Milano" )
+					);
+			addresses.remove( new Address( "via Pierce", null ) );
+		} );
+
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, thePerson.getId() );
+			Set<Address> addresses = person.getAddresses();
+			assertThat( addresses )
+					.containsExactlyInAnyOrder(
+							new Address( "via Cartesio", "Milano" )
+					);
+			addresses.remove( new Address( "via Pierce", null ) );
+		} );
+	}
+
+	@Entity(name = "Person")
+	@Table(name = "Person")
+	static class Person {
+		@Id
+		private Integer id;
+		private String name;
+
+		@ElementCollection(fetch = FetchType.EAGER)
+		private Set<Address> addresses;
+
+		public Person() {
+		}
+
+		public Person(Integer id, String name, Collection<Address> addresses) {
+			this.id = id;
+			this.name = name;
+			this.addresses = new HashSet<>( addresses );
+		}
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+
+		public Set<Address> getAddresses() {
+			return addresses;
+		}
+
+		public void setAddresses(Set<Address> addresses) {
+			this.addresses = addresses;
+		}
+
+	}
+
+	@Embeddable
+	public static class Address {
+		@Basic(optional = false)
+		private String street;
+		private String city;
+
+		public Address() {
+		}
+
+		public Address(String street, String city) {
+			this.street = street;
+			this.city = city;
+		}
+
+		@Override
+		public boolean equals(Object o) {
+			if ( this == o ) {
+				return true;
+			}
+			if ( o == null || getClass() != o.getClass() ) {
+				return false;
+			}
+			Address address = (Address) o;
+			return Objects.equals( street, address.street ) && Objects.equals( city, address.city );
+		}
+
+		@Override
+		public int hashCode() {
+			return Objects.hash( street, city );
+		}
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/embeddable/EmbeddableWithNotOprionalAttributeAsElementCollectionUpdateTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/embeddable/EmbeddableWithNotOprionalAttributeAsElementCollectionUpdateTest.java
new file mode 100644
index 0000000000..cb5c7661b8
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/embeddable/EmbeddableWithNotOprionalAttributeAsElementCollectionUpdateTest.java
@@ -0,0 +1,147 @@
+package org.hibernate.orm.test.embeddable;
+
+import java.util.Arrays;
+import java.util.Collection;
+import java.util.HashSet;
+import java.util.Objects;
+import java.util.Set;
+
+import org.hibernate.testing.TestForIssue;
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.Basic;
+import jakarta.persistence.ElementCollection;
+import jakarta.persistence.Embeddable;
+import jakarta.persistence.Entity;
+import jakarta.persistence.FetchType;
+import jakarta.persistence.Id;
+import jakarta.persistence.Table;
+import org.assertj.core.api.Assertions;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+@DomainModel(annotatedClasses = EmbeddableWithNotOprionalAttributeAsElementCollectionUpdateTest.Person.class)
+@SessionFactory
+@TestForIssue(jiraKey = "HHH-16297")
+public class EmbeddableWithNotOprionalAttributeAsElementCollectionUpdateTest {
+
+	private Person thePerson;
+
+	@BeforeAll
+	public void prepare(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			Set<Address> addresses = new HashSet<>( Arrays.asList(
+					new Address( "via milano", "Roma" ),
+					new Address( "via Cartesio", "Milano" )
+			) );
+			thePerson = new Person( 7242000, "Claude", addresses );
+			session.persist( thePerson );
+		} );
+	}
+
+	@Test
+	public void removeElementAndAddNewOne(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			Person foundPerson = session.find( Person.class, thePerson.getId() );
+			Assertions.assertThat( foundPerson ).isNotNull();
+			Set<Address> addresses = foundPerson.getAddresses();
+			addresses.remove( new Address( "via milano", "Roma" ) );
+			addresses.add( new Address( "via Pierce", "Milano" ) );
+			assertThat( addresses )
+					.containsExactlyInAnyOrder(
+							new Address( "via Pierce", "Milano" ),
+							new Address( "via Cartesio", "Milano" )
+					);
+		} );
+		scope.inTransaction( session -> {
+			Person person = session.find( Person.class, thePerson.getId() );
+			assertThat( person.getAddresses() )
+					.containsExactlyInAnyOrder(
+							new Address( "via Pierce", "Milano" ),
+							new Address( "via Cartesio", "Milano" )
+					);
+		} );
+	}
+
+	@Entity(name = "Person")
+	@Table(name = "Person")
+	static class Person {
+		@Id
+		private Integer id;
+		private String name;
+
+		@ElementCollection(fetch = FetchType.EAGER)
+		private Set<Address> addresses;
+
+		public Person() {
+		}
+
+		public Person(Integer id, String name, Collection<Address> addresses) {
+			this.id = id;
+			this.name = name;
+			this.addresses = new HashSet<>( addresses );
+		}
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+
+		public Set<Address> getAddresses() {
+			return addresses;
+		}
+
+		public void setAddresses(Set<Address> addresses) {
+			this.addresses = addresses;
+		}
+
+	}
+
+	@Embeddable
+	public static class Address {
+		@Basic(optional = false)
+		private String street;
+		@Basic(optional = false)
+		private String city;
+
+		public Address() {
+		}
+
+		public Address(String street, String city) {
+			this.street = street;
+			this.city = city;
+		}
+
+		@Override
+		public boolean equals(Object o) {
+			if ( this == o ) {
+				return true;
+			}
+			if ( o == null || getClass() != o.getClass() ) {
+				return false;
+			}
+			Address address = (Address) o;
+			return Objects.equals( street, address.street ) && Objects.equals( city, address.city );
+		}
+
+		@Override
+		public int hashCode() {
+			return Objects.hash( street, city );
+		}
+	}
+}