diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/locking/RemoveEntityTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/locking/RemoveEntityTest.java
new file mode 100644
index 0000000000..2b6fbe44c8
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/locking/RemoveEntityTest.java
@@ -0,0 +1,187 @@
+package org.hibernate.orm.test.locking;
+
+import java.util.Collection;
+import java.util.HashSet;
+import java.util.List;
+import java.util.Set;
+
+import org.hibernate.annotations.DynamicUpdate;
+import org.hibernate.annotations.OptimisticLockType;
+import org.hibernate.annotations.OptimisticLocking;
+
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.JiraKey;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.Column;
+import jakarta.persistence.Entity;
+import jakarta.persistence.FetchType;
+import jakarta.persistence.GeneratedValue;
+import jakarta.persistence.GenerationType;
+import jakarta.persistence.Id;
+import jakarta.persistence.JoinColumn;
+import jakarta.persistence.ManyToOne;
+import jakarta.persistence.OneToMany;
+import jakarta.persistence.Table;
+import jakarta.persistence.UniqueConstraint;
+
+import static org.assertj.core.api.AssertionsForClassTypes.assertThat;
+
+@DomainModel(
+		annotatedClasses = {
+				RemoveEntityTest.EmployeeEntity.class,
+				RemoveEntityTest.LinkEntity.class
+		}
+)
+@SessionFactory
+@JiraKey("HHH-16816")
+public class RemoveEntityTest {
+
+	private static final String EMPLOYEE_TO_DELETE_MAIL = "demo-user@mail.com";
+
+	@BeforeEach
+	public void setUp(SessionFactoryScope scope) {
+		scope.inTransaction(
+				session -> {
+					EmployeeEntity emp = new EmployeeEntity();
+					emp.setEmail( EMPLOYEE_TO_DELETE_MAIL );
+					session.save( emp );
+
+					LinkEntity linkEntity = new LinkEntity();
+					linkEntity.setEmployeeId( emp.getEmployeeId() );
+					session.save( linkEntity );
+
+					Set<LinkEntity> link = Set.of( linkEntity );
+					emp.setFolderLink( link );
+					session.save( emp );
+
+					emp = new EmployeeEntity();
+					emp.setEmail( "demo-user2@mail.com" );
+					session.save( emp );
+				}
+		);
+	}
+
+	@Test
+	public void testDelete(SessionFactoryScope scope) {
+		scope.inTransaction(
+				session -> {
+					EmployeeEntity employee = session.createQuery(
+							"FROM EmployeeEntity e where e.email = :mail",
+							EmployeeEntity.class
+					).setParameter( "mail", EMPLOYEE_TO_DELETE_MAIL ).getSingleResult();
+
+					assertThat( employee ).isNotNull();
+
+					List<LinkEntity> links = session.createQuery( "FROM LinkEntity", LinkEntity.class ).list();
+					assertThat( links.size() ).isEqualTo( 1 );
+
+					LinkEntity linkEntity = links.get( 0 );
+					assertThat( linkEntity.getEmployeeId() ).isEqualTo( employee.getEmployeeId() );
+
+					session.remove( linkEntity );
+					session.remove( employee );
+				}
+		);
+
+		scope.inTransaction(
+				session -> {
+					List<EmployeeEntity> employees = session.createQuery(
+							"FROM EmployeeEntity e where e.email = :mail",
+							EmployeeEntity.class
+					).setParameter( "mail", EMPLOYEE_TO_DELETE_MAIL ).getResultList();
+
+					assertThat( employees.size() ).isEqualTo( 0 );
+
+					List<LinkEntity> links = session.createQuery( "FROM LinkEntity", LinkEntity.class ).list();
+					assertThat( links.size() ).isEqualTo( 0 );
+				}
+		);
+	}
+
+	@Entity(name = "EmployeeEntity")
+	@Table(name = "Employee", uniqueConstraints = {
+			@UniqueConstraint(columnNames = "ID"),
+			@UniqueConstraint(columnNames = "EMAIL")
+	})
+	public static class EmployeeEntity {
+
+		@Id
+		@GeneratedValue(strategy = GenerationType.IDENTITY)
+		@Column(name = "ID")
+		private Integer employeeId;
+
+		@Column(name = "EMAIL", unique = true, nullable = false, length = 100)
+		private String email;
+
+		@OneToMany(targetEntity = LinkEntity.class, mappedBy = "employee")
+		final Set<LinkEntity> folderLink = new HashSet<>();
+
+		public Collection<LinkEntity> getFolderLink() {
+			return folderLink;
+		}
+
+		public void setFolderLink(Collection<LinkEntity> folderLink) {
+			final HashSet<LinkEntity> changed = new HashSet<>( folderLink );
+			changed.removeAll( this.folderLink );
+			changed.forEach( added -> added.setEmployee( this ) );
+			changed.clear();
+			changed.addAll( this.folderLink );
+			changed.removeAll( folderLink );
+			changed.forEach( removed -> removed.setEmployee( null ) );
+		}
+
+		public Integer getEmployeeId() {
+			return employeeId;
+		}
+
+		public void setEmployeeId(Integer employeeId) {
+			this.employeeId = employeeId;
+		}
+
+		public String getEmail() {
+			return email;
+		}
+
+		public void setEmail(String email) {
+			this.email = email;
+		}
+	}
+
+	@Entity(name = "LinkEntity")
+	@OptimisticLocking(type = OptimisticLockType.DIRTY)
+	@DynamicUpdate
+	@Table(name = "Link")
+	public static class LinkEntity {
+
+		@Id
+		@Column(name = "EMPLOYEE_ID")
+		private Integer employeeId;
+
+		private String name;
+
+		@ManyToOne(fetch = FetchType.LAZY)
+		@JoinColumn(name = "EMPLOYEE_ID", insertable = false, updatable = false)
+		EmployeeEntity employee;
+
+		public EmployeeEntity getEmployee() {
+			return employee;
+		}
+
+		public void setEmployee(EmployeeEntity realFolder) {
+			this.employee = realFolder;
+		}
+
+		public Integer getEmployeeId() {
+			return employeeId;
+		}
+
+		public void setEmployeeId(Integer employeeId) {
+			this.employeeId = employeeId;
+		}
+	}
+
+}