diff --git a/hibernate-core/src/test/java/org/hibernate/test/hql/size/WhereClauseOrderBySizeTest.java b/hibernate-core/src/test/java/org/hibernate/test/hql/size/WhereClauseOrderBySizeTest.java
new file mode 100644
index 0000000000..81d7170b07
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/test/hql/size/WhereClauseOrderBySizeTest.java
@@ -0,0 +1,195 @@
+/*
+ * Hibernate, Relational Persistence for Idiomatic Java
+ *
+ * License: GNU Lesser General Public License (LGPL), version 2.1 or later.
+ * See the lgpl.txt file in the root directory or <http://www.gnu.org/licenses/lgpl-2.1.html>.
+ */
+
+package org.hibernate.test.hql.size;
+
+import org.hibernate.annotations.ResultCheckStyle;
+import org.hibernate.annotations.SQLDelete;
+import org.hibernate.annotations.Where;
+import org.hibernate.jpa.test.BaseEntityManagerFunctionalTestCase;
+
+import org.hibernate.testing.TestForIssue;
+import org.junit.After;
+import org.junit.Test;
+
+import javax.persistence.CascadeType;
+import javax.persistence.Entity;
+import javax.persistence.FetchType;
+import javax.persistence.GeneratedValue;
+import javax.persistence.Id;
+import javax.persistence.ManyToOne;
+import javax.persistence.OneToMany;
+import javax.persistence.TypedQuery;
+import java.util.ArrayList;
+import java.util.Arrays;
+import java.util.List;
+
+import static org.hibernate.testing.transaction.TransactionUtil.doInJPA;
+import static org.junit.Assert.assertEquals;
+
+@TestForIssue(jiraKey = "HHH-14585")
+public class WhereClauseOrderBySizeTest extends BaseEntityManagerFunctionalTestCase {
+
+	@Override
+	protected Class<?>[] getAnnotatedClasses() {
+		return new Class<?>[] { Person.class, Book.class };
+	}
+
+	@Test
+	public void testSizeAsOrderByExpression() {
+		doInJPA(
+				this::entityManagerFactory,
+				entityManager -> {
+					// initial situation: Alice has 1 book, Bob none
+					final Person alice = new Person( "Alice" );
+					entityManager.persist( alice );
+
+					final Book book1 = new Book();
+					book1.setOwner( alice );
+					entityManager.persist( book1 );
+
+					final Person bob = new Person( "Bob" );
+					entityManager.persist( bob );
+
+					final TypedQuery<Person> orderByBroken = entityManager.createQuery(
+							"SELECT p FROM Person p ORDER BY size(p.books) DESC",
+							Person.class
+					);
+					final TypedQuery<Person> orderByWorking = entityManager.createQuery(
+							"SELECT p FROM Person p ORDER BY p.books.size DESC",
+							Person.class
+					);
+
+					List<Person> dbPeopleBroken = orderByBroken.getResultList();
+					List<Person> dbPeopleWorking = orderByWorking.getResultList();
+					assertEquals( Arrays.asList( alice, bob ), dbPeopleWorking );
+					assertEquals( dbPeopleWorking, dbPeopleBroken );
+
+					// add 2 books to Bob
+					final Book book2 = new Book();
+					book2.setOwner( bob );
+					entityManager.persist( book2 );
+
+					final Book book3 = new Book();
+					book3.setOwner( bob );
+					entityManager.persist( book3 );
+
+					dbPeopleBroken = orderByBroken.getResultList();
+					dbPeopleWorking = orderByWorking.getResultList();
+					assertEquals( Arrays.asList( bob, alice ), dbPeopleWorking );
+					assertEquals( dbPeopleWorking, dbPeopleBroken );
+
+					// remove (soft-deleting) both Bob's books
+					entityManager.remove( book2 );
+					entityManager.remove( book3 );
+
+					// result lists are not equal anymore
+					dbPeopleBroken = orderByBroken.getResultList();
+					dbPeopleWorking = orderByWorking.getResultList();
+					assertEquals( Arrays.asList( alice, bob ), dbPeopleWorking );
+					assertEquals( dbPeopleWorking, dbPeopleBroken );
+				}
+		);
+	}
+
+	@After
+	public void cleanupDatabase() {
+		doInJPA(
+				this::entityManagerFactory,
+				entityManager -> {
+					for ( Book book : entityManager.createQuery( "from Book", Book.class ).getResultList() ) {
+						entityManager.remove( book );
+					}
+					for ( Person person : entityManager.createQuery( "from Person", Person.class ).getResultList() ) {
+						entityManager.remove( person );
+					}
+				}
+		);
+	}
+
+	@Entity(name = "Person")
+	public static class Person {
+		@Id
+		@GeneratedValue
+		private Long id;
+		private String name;
+		@OneToMany(mappedBy = "owner", fetch = FetchType.LAZY, cascade = CascadeType.REMOVE)
+		private List<Book> books = new ArrayList<>();
+
+		public Person(String name) {
+			this.name = name;
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+
+		public List<Book> getBooks() {
+			return books;
+		}
+
+		public void setBooks(List<Book> books) {
+			this.books = books;
+		}
+
+		@Override
+		public String toString() {
+			return "Person{" +
+					"id=" + id +
+					", name='" + name + '\'' +
+					'}';
+		}
+	}
+
+	@Entity(name = "Book")
+	@SQLDelete(sql = "UPDATE Book SET deleted = true WHERE id = ?", check = ResultCheckStyle.COUNT)
+	@Where(clause = "deleted = false")
+	public static class Book {
+		@Id
+		@GeneratedValue
+		private Long id;
+		private Boolean deleted = false;
+		@ManyToOne
+		private Person owner;
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public Boolean getDeleted() {
+			return deleted;
+		}
+
+		public void setDeleted(Boolean deleted) {
+			this.deleted = deleted;
+		}
+
+		public Person getOwner() {
+			return owner;
+		}
+
+		public void setOwner(Person owner) {
+			this.owner = owner;
+		}
+	}
+}