diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/id/ReSaveReferencedDeletedEntity.java b/hibernate-core/src/test/java/org/hibernate/orm/test/id/ReSaveReferencedDeletedEntity.java
new file mode 100644
index 0000000000..855055d7cb
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/id/ReSaveReferencedDeletedEntity.java
@@ -0,0 +1,112 @@
+/*
+ * SPDX-License-Identifier: LGPL-2.1-or-later
+ * Copyright Red Hat Inc. and Hibernate Authors
+ */
+package org.hibernate.orm.test.id;
+
+import org.hibernate.cfg.AvailableSettings;
+import org.hibernate.cfg.Configuration;
+import org.hibernate.testing.orm.junit.JiraKey;
+import org.hibernate.testing.junit4.BaseCoreFunctionalTestCase;
+import org.junit.Test;
+
+import jakarta.persistence.*;
+
+import static org.hibernate.testing.transaction.TransactionUtil.doInHibernate;
+
+public class ReSaveReferencedDeletedEntity extends BaseCoreFunctionalTestCase {
+	@Override
+	protected Class<?>[] getAnnotatedClasses() {
+		return new Class<?>[] { Child.class, Parent.class };
+	}
+
+	@Override
+	protected void configure(Configuration configuration) {
+		super.configure( configuration );
+		configuration.setProperty( AvailableSettings.USE_IDENTIFIER_ROLLBACK, "true" );
+	}
+
+	@Test
+	@JiraKey("HHH-14416")
+	public void testReSaveDeletedEntity() {
+		doInHibernate( this::sessionFactory, session -> {
+			Parent parent = new Parent();
+
+			Child child = new Child();
+			parent.setChild( child );
+
+			session.persist( parent );
+
+			parent.setChild( null );
+			session.remove(child);
+
+			session.flush();
+
+			parent.setChild( child );
+			session.persist(child);
+		} );
+	}
+
+	@Test
+	@JiraKey("HHH-14416")
+	public void testReSaveDeletedEntityWithDetach() {
+		doInHibernate( this::sessionFactory, session -> {
+			Parent parent = new Parent();
+
+			Child child = new Child();
+			parent.setChild( child );
+
+			session.persist( parent );
+
+			parent.setChild( null );
+			session.remove(child);
+
+			session.flush();
+			session.detach(child);
+
+			parent.setChild( child );
+			session.persist(child);
+		} );
+	}
+
+	@Entity(name = "Child")
+	public static class Child {
+		@Id
+		@GeneratedValue(strategy = GenerationType.IDENTITY)
+		private Integer id;
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+	}
+
+	@Entity(name = "Parent")
+	public static class Parent {
+		@Id
+		@GeneratedValue(strategy = GenerationType.IDENTITY)
+		private Integer id;
+
+		@OneToOne(cascade = CascadeType.ALL)
+		private Child child;
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		public Child getChild() {
+			return child;
+		}
+
+		public void setChild(Child child) {
+			this.child = child;
+		}
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/id/ReSaveReferencedDeletedEntityJPA.java b/hibernate-core/src/test/java/org/hibernate/orm/test/id/ReSaveReferencedDeletedEntityJPA.java
new file mode 100644
index 0000000000..5de83db03f
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/id/ReSaveReferencedDeletedEntityJPA.java
@@ -0,0 +1,122 @@
+/*
+ * SPDX-License-Identifier: LGPL-2.1-or-later
+ * Copyright Red Hat Inc. and Hibernate Authors
+ */
+package org.hibernate.orm.test.id;
+
+import org.hibernate.cfg.AvailableSettings;
+import org.hibernate.testing.orm.junit.JiraKey;
+import org.hibernate.orm.test.jpa.BaseEntityManagerFunctionalTestCase;
+import org.junit.Test;
+
+import jakarta.persistence.*;
+
+import java.util.Map;
+
+public class ReSaveReferencedDeletedEntityJPA extends BaseEntityManagerFunctionalTestCase {
+	@Override
+	protected Class<?>[] getAnnotatedClasses() {
+		return new Class<?>[] { Child.class, Parent.class };
+	}
+
+	@Override
+	protected Map<Object, Object> buildSettings() {
+		Map<Object, Object> settings = super.buildSettings();
+		settings.put( AvailableSettings.USE_IDENTIFIER_ROLLBACK, "true"  );
+		return settings;
+	}
+
+	@Test
+	@ JiraKey("HHH-14416")
+	public void testRefreshUnDeletedEntityWithReferencesJPA() {
+		EntityManager em = getOrCreateEntityManager();
+		em.getTransaction().begin();
+
+		Parent parent = new Parent();
+		parent.setId(1);
+
+		Child child = new Child();
+		child.setId(2);
+		parent.setChild( child );
+
+		em.persist( parent );
+
+		em.flush();
+
+		em.remove( parent );
+
+		em.flush();
+
+		em.detach( parent );
+
+		em.persist( parent );
+
+		em.flush();
+
+		em.refresh( child );
+
+		em.getTransaction().commit();
+	}
+
+	@Test
+	@JiraKey("HHH-14416")
+	public void testReSaveDeletedEntityWithReferencesJPA() {
+		EntityManager em = getOrCreateEntityManager();
+		em.getTransaction().begin();
+
+		Parent parent = new Parent();
+		parent.setId(1);
+
+		Child child = new Child();
+		child.setId(2);
+		parent.setChild( child );
+
+		em.persist( parent );
+
+		parent.setChild( null );
+		em.remove( child );
+
+		em.persist( child );
+
+		em.getTransaction().commit();
+	}
+
+	@Entity(name = "Child")
+	public static class Child {
+		@Id
+		private Integer id;
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+	}
+
+	@Entity(name = "Parent")
+	public static class Parent {
+		@Id
+		private Integer id;
+
+		@OneToOne(cascade = CascadeType.ALL)
+		private Child child;
+
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		public Child getChild() {
+			return child;
+		}
+
+		public void setChild(Child child) {
+			this.child = child;
+		}
+	}
+}