diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/query/EntityValuedPathInSubqueryTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/query/EntityValuedPathInSubqueryTest.java
new file mode 100644
index 0000000000..461bcd30d9
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/query/EntityValuedPathInSubqueryTest.java
@@ -0,0 +1,235 @@
+/*
+ * 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.orm.test.query;
+
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.Jira;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.AfterAll;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.Entity;
+import jakarta.persistence.GeneratedValue;
+import jakarta.persistence.Id;
+import jakarta.persistence.JoinColumn;
+import jakarta.persistence.ManyToOne;
+import jakarta.persistence.criteria.CriteriaBuilder;
+import jakarta.persistence.criteria.CriteriaQuery;
+import jakarta.persistence.criteria.Root;
+import jakarta.persistence.criteria.Subquery;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * @author Marco Belladelli
+ */
+@SessionFactory
+@DomainModel( annotatedClasses = EntityValuedPathInSubqueryTest.EntityA.class )
+@Jira( "https://hibernate.atlassian.net/browse/HHH-16397" )
+public class EntityValuedPathInSubqueryTest {
+	@BeforeAll
+	public void setUp(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final EntityA entityA1 = new EntityA( "entitya_1", 1, null );
+			session.persist( entityA1 );
+			session.persist( new EntityA( "entitya_2", 2, entityA1 ) );
+		} );
+	}
+
+	@AfterAll
+	public void tearDown(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			session.createMutationQuery( "update EntityA set reference = null" ).executeUpdate();
+			session.createMutationQuery( "delete from EntityA" ).executeUpdate();
+		} );
+	}
+
+	@Test
+	public void testReference(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final String result = session.createQuery(
+					"select a.name from EntityA a where a.amount = " +
+					"(select max(b.amount) from EntityA b where a.reference is null and b.reference is null)",
+					String.class
+			).getSingleResult();
+			assertThat( result ).isEqualTo( "entitya_1" );
+		} );
+	}
+
+	@Test
+	public void testReferenceSelectEntity(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final EntityA result = session.createQuery(
+					"select a from EntityA a where a.amount = " +
+					"(select max(b.amount) from EntityA b where a.reference is null and b.reference is null)",
+					EntityA.class
+			).getSingleResult();
+			assertThat( result.getName() ).isEqualTo( "entitya_1" );
+		} );
+	}
+
+	@Test
+	public void testExplicitFkReference(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final String result = session.createQuery(
+					"select a.name from EntityA a where a.amount = " +
+					"(select max(b.amount) from EntityA b where a.reference.id is null and b.reference.id is null)",
+					String.class
+			).getSingleResult();
+			assertThat( result ).isEqualTo( "entitya_1" );
+		} );
+	}
+
+	@Test
+	public void testImplicitJoin(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final String result = session.createQuery(
+					"select a.name from EntityA a where a.amount = " +
+					"(select max(b.amount) from EntityA b where a.reference.name = 'entitya_1' and b.reference is not null)",
+					String.class
+			).getSingleResult();
+			assertThat( result ).isEqualTo( "entitya_2" );
+		} );
+	}
+
+	@Test
+	public void testImplicitJoinSelectReference(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final EntityA result = session.createQuery(
+					"select a.reference from EntityA a where a.amount = " +
+					"(select max(b.amount) from EntityA b where a.reference.name = 'entitya_1' and b.reference is not null)",
+					EntityA.class
+			).getSingleResult();
+			assertThat( result.getName() ).isEqualTo( "entitya_1" );
+		} );
+	}
+
+	@Test
+	public void testReferenceCriteria(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final CriteriaBuilder cb = session.getCriteriaBuilder();
+			final CriteriaQuery<String> query = cb.createQuery( String.class );
+			final Root<EntityA> root = query.from( EntityA.class );
+			// subquery with correlated root
+			final Subquery<Integer> subquery = query.subquery( Integer.class );
+			final Root<EntityA> correlatedRoot = subquery.correlate( root );
+			final Root<EntityA> subRoot = subquery.from( EntityA.class );
+			subquery.select( cb.max( subRoot.get( "amount" ) ) ).where( cb.and(
+					cb.isNull( correlatedRoot.get( "reference" ) ),
+					cb.isNull( subRoot.get( "reference" ) )
+			) );
+			// query
+			query.select( root.get( "name" ) ).where( cb.equal( root.get( "amount" ), subquery ) );
+			final String result = session.createQuery( query ).getSingleResult();
+			assertThat( result ).isEqualTo( "entitya_1" );
+		} );
+	}
+
+	@Test
+	public void testReferenceSelectEntityCriteria(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final CriteriaBuilder cb = session.getCriteriaBuilder();
+			final CriteriaQuery<EntityA> query = cb.createQuery( EntityA.class );
+			final Root<EntityA> root = query.from( EntityA.class );
+			// subquery with correlated root
+			final Subquery<Integer> subquery = query.subquery( Integer.class );
+			final Root<EntityA> correlatedRoot = subquery.correlate( root );
+			final Root<EntityA> subRoot = subquery.from( EntityA.class );
+			subquery.select( cb.max( subRoot.get( "amount" ) ) ).where( cb.and(
+					cb.isNull( correlatedRoot.get( "reference" ) ),
+					cb.isNull( subRoot.get( "reference" ) )
+			) );
+			// query
+			query.select( root ).where( cb.equal( root.get( "amount" ), subquery ) );
+			final EntityA result = session.createQuery( query ).getSingleResult();
+			assertThat( result.getName() ).isEqualTo( "entitya_1" );
+		} );
+	}
+
+	@Test
+	public void testExplicitFkReferenceCriteria(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final CriteriaBuilder cb = session.getCriteriaBuilder();
+			final CriteriaQuery<String> query = cb.createQuery( String.class );
+			final Root<EntityA> root = query.from( EntityA.class );
+			// subquery with correlated root
+			final Subquery<Integer> subquery = query.subquery( Integer.class );
+			final Root<EntityA> correlatedRoot = subquery.correlate( root );
+			final Root<EntityA> subRoot = subquery.from( EntityA.class );
+			subquery.select( cb.max( subRoot.get( "amount" ) ) ).where( cb.and(
+					cb.isNull( correlatedRoot.get( "reference" ).get( "id" ) ),
+					cb.isNull( subRoot.get( "reference" ).get( "id" ) )
+			) );
+			// query
+			query.select( root.get( "name" ) ).where( cb.equal( root.get( "amount" ), subquery ) );
+			final String result = session.createQuery( query ).getSingleResult();
+			assertThat( result ).isEqualTo( "entitya_1" );
+		} );
+	}
+
+	@Test
+	public void testImplicitJoinCriteria(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final CriteriaBuilder cb = session.getCriteriaBuilder();
+			final CriteriaQuery<String> query = cb.createQuery( String.class );
+			final Root<EntityA> root = query.from( EntityA.class );
+
+			final Subquery<Integer> subquery = query.subquery( Integer.class );
+			final Root<EntityA> subRoot = subquery.from( EntityA.class );
+			subquery.select( cb.max( subRoot.get( "amount" ) ) ).where( cb.and(
+					cb.equal( root.get( "reference" ).get( "name" ), "entitya_1" ),
+					cb.isNotNull( subRoot.get( "reference" ) )
+			) );
+
+			query.select( root.get( "name" ) ).where( cb.equal( root.get( "amount" ), subquery ) );
+			final String result = session.createQuery( query ).getSingleResult();
+			assertThat( result ).isEqualTo( "entitya_2" );
+		} );
+	}
+
+	@Entity( name = "EntityA" )
+	public static class EntityA {
+		@Id
+		@GeneratedValue
+		private Long id;
+
+		private String name;
+
+		private Integer amount;
+
+		@ManyToOne
+		@JoinColumn( name = "reference" )
+		private EntityA reference;
+
+		public EntityA() {
+		}
+
+		public EntityA(String name, Integer amount, EntityA reference) {
+			this.name = name;
+			this.amount = amount;
+			this.reference = reference;
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public String getName() {
+			return name;
+		}
+
+		public Integer getAmount() {
+			return amount;
+		}
+
+		public EntityA getReference() {
+			return reference;
+		}
+	}
+}