diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/query/order/OrderTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/query/order/OrderTest.java
index d9ef9f0e1a..4230686838 100644
--- a/hibernate-core/src/test/java/org/hibernate/orm/test/query/order/OrderTest.java
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/query/order/OrderTest.java
@@ -14,7 +14,10 @@
 
 import static java.util.stream.Collectors.toList;
 import static org.hibernate.query.Order.asc;
+import static org.hibernate.query.Order.by;
 import static org.hibernate.query.Order.desc;
+import static org.hibernate.query.SortDirection.ASCENDING;
+import static org.hibernate.query.SortDirection.DESCENDING;
 import static org.junit.jupiter.api.Assertions.assertEquals;
 
 @SessionFactory
@@ -254,6 +257,208 @@ public class OrderTest {
         });
     }
 
+    @Test void testAscendingDescendingCaseInsensitive(SessionFactoryScope scope) {
+        scope.inTransaction( session -> session.createMutationQuery("delete Book").executeUpdate() );
+        scope.inTransaction( session -> {
+            session.persist(new Book("9781932394153", "Hibernate in Action"));
+            session.persist(new Book("9781617290459", "Java Persistence with Hibernate"));
+        });
+        EntityDomainType<Book> bookType = scope.getSessionFactory().getJpaMetamodel().findEntityType(Book.class);
+        SingularAttribute<? super Book, ?> title = bookType.findSingularAttribute("title");
+        SingularAttribute<? super Book, ?> isbn = bookType.findSingularAttribute("isbn");
+        scope.inSession(session -> {
+            List<String> titlesAsc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(asc(title).ignoringCase())
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesAsc.get(0));
+            assertEquals("Java Persistence with Hibernate", titlesAsc.get(1));
+
+            List<String> titlesDesc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(desc(title).ignoringCase())
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesDesc.get(1));
+            assertEquals("Java Persistence with Hibernate", titlesDesc.get(0));
+
+            List<String> isbnAsc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(List.of(asc(isbn).ignoringCase(), desc(title).ignoringCase()))
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnAsc.get(1));
+            assertEquals("Java Persistence with Hibernate", isbnAsc.get(0));
+
+            List<String> isbnDesc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(List.of(desc(isbn).ignoringCase(), desc(title).ignoringCase()))
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnDesc.get(0));
+            assertEquals("Java Persistence with Hibernate", isbnDesc.get(1));
+
+//            titlesAsc = session.createSelectionQuery("from Book order by isbn asc", Book.class)
+//                    .setOrder(asc(title))
+//                    .getResultList()
+//                    .stream().map(book -> book.title)
+//                    .collect(toList());
+//            assertEquals("Hibernate in Action", titlesAsc.get(1));
+//            assertEquals("Java Persistence with Hibernate", titlesAsc.get(0));
+            titlesAsc = session.createSelectionQuery("from Book order by isbn asc", Book.class)
+//                    .setOrder(emptyList())
+                    .setOrder(asc(title).ignoringCase())
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesAsc.get(0));
+            assertEquals("Java Persistence with Hibernate", titlesAsc.get(1));
+        });
+    }
+
+    @Test void testAscendingDescendingCaseInsensitiveLongForm(SessionFactoryScope scope) {
+        scope.inTransaction( session -> session.createMutationQuery("delete Book").executeUpdate() );
+        scope.inTransaction( session -> {
+            session.persist(new Book("9781932394153", "Hibernate in Action"));
+            session.persist(new Book("9781617290459", "Java Persistence with Hibernate"));
+        });
+        EntityDomainType<Book> bookType = scope.getSessionFactory().getJpaMetamodel().findEntityType(Book.class);
+        SingularAttribute<? super Book, ?> title = bookType.findSingularAttribute("title");
+        SingularAttribute<? super Book, ?> isbn = bookType.findSingularAttribute("isbn");
+        scope.inSession(session -> {
+            List<String> titlesAsc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(by(title, ASCENDING, true))
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesAsc.get(0));
+            assertEquals("Java Persistence with Hibernate", titlesAsc.get(1));
+
+            List<String> titlesDesc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(by(title, DESCENDING, true))
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesDesc.get(1));
+            assertEquals("Java Persistence with Hibernate", titlesDesc.get(0));
+
+            List<String> isbnAsc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(List.of(by(isbn, ASCENDING, true), by(title, DESCENDING, true)))
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnAsc.get(1));
+            assertEquals("Java Persistence with Hibernate", isbnAsc.get(0));
+
+            List<String> isbnDesc = session.createSelectionQuery("from Book", Book.class)
+                    .setOrder(List.of(by(isbn, DESCENDING, true), by(title, DESCENDING, true)))
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnDesc.get(0));
+            assertEquals("Java Persistence with Hibernate", isbnDesc.get(1));
+
+//            titlesAsc = session.createSelectionQuery("from Book order by isbn asc", Book.class)
+//                    .setOrder(asc(title))
+//                    .getResultList()
+//                    .stream().map(book -> book.title)
+//                    .collect(toList());
+//            assertEquals("Hibernate in Action", titlesAsc.get(1));
+//            assertEquals("Java Persistence with Hibernate", titlesAsc.get(0));
+            titlesAsc = session.createSelectionQuery("from Book order by isbn asc", Book.class)
+//                    .setOrder(emptyList())
+                    .setOrder(by(title, ASCENDING, true))
+                    .getResultList()
+                    .stream().map(book -> book.title)
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesAsc.get(0));
+            assertEquals("Java Persistence with Hibernate", titlesAsc.get(1));
+        });
+    }
+
+    @Test void testAscendingDescendingBySelectElementCaseInsensitive(SessionFactoryScope scope) {
+        scope.inTransaction( session -> session.createMutationQuery("delete Book").executeUpdate() );
+        scope.inTransaction( session -> {
+            session.persist(new Book("9781932394153", "Hibernate in Action"));
+            session.persist(new Book("9781617290459", "Java Persistence with Hibernate"));
+        });
+        scope.inSession(session -> {
+            List<?> titlesAsc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(asc(2).ignoringCase())
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesAsc.get(0));
+            assertEquals("Java Persistence with Hibernate", titlesAsc.get(1));
+
+            List<?> titlesDesc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(desc(2).ignoringCase())
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesDesc.get(1));
+            assertEquals("Java Persistence with Hibernate", titlesDesc.get(0));
+
+            List<?> isbnAsc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(List.of(asc(1).ignoringCase(), desc(2).ignoringCase()))
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnAsc.get(1));
+            assertEquals("Java Persistence with Hibernate", isbnAsc.get(0));
+
+            List<?> isbnDesc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(List.of(desc(1).ignoringCase(), desc(2).ignoringCase()))
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnDesc.get(0));
+            assertEquals("Java Persistence with Hibernate", isbnDesc.get(1));
+        });
+    }
+
+    @Test void testAscendingDescendingBySelectElementCaseInsensitiveLongForm(SessionFactoryScope scope) {
+        scope.inTransaction( session -> session.createMutationQuery("delete Book").executeUpdate() );
+        scope.inTransaction( session -> {
+            session.persist(new Book("9781932394153", "Hibernate in Action"));
+            session.persist(new Book("9781617290459", "Java Persistence with Hibernate"));
+        });
+        scope.inSession(session -> {
+            List<?> titlesAsc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(by(2, ASCENDING, true))
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesAsc.get(0));
+            assertEquals("Java Persistence with Hibernate", titlesAsc.get(1));
+
+            List<?> titlesDesc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(by(2, DESCENDING, true))
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", titlesDesc.get(1));
+            assertEquals("Java Persistence with Hibernate", titlesDesc.get(0));
+
+            List<?> isbnAsc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(List.of(by(1, ASCENDING, true), by(2, DESCENDING, true)))
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnAsc.get(1));
+            assertEquals("Java Persistence with Hibernate", isbnAsc.get(0));
+
+            List<?> isbnDesc = session.createSelectionQuery("select isbn, title from Book", Object[].class)
+                    .setOrder(List.of(by(1, DESCENDING, true), by(2, DESCENDING, true)))
+                    .getResultList()
+                    .stream().map(book -> book[1])
+                    .collect(toList());
+            assertEquals("Hibernate in Action", isbnDesc.get(0));
+            assertEquals("Java Persistence with Hibernate", isbnDesc.get(1));
+        });
+    }
+
     @Entity(name="Book")
     static class Book {
         @Id String isbn;