diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/subquery/SubqueryMultipleLeftJoinsTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/subquery/SubqueryMultipleLeftJoinsTest.java
new file mode 100644
index 0000000000..3d579dc90e
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/subquery/SubqueryMultipleLeftJoinsTest.java
@@ -0,0 +1,225 @@
+/*
+ * 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.jpa.criteria.subquery;
+
+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.Id;
+import jakarta.persistence.ManyToOne;
+import jakarta.persistence.criteria.CriteriaBuilder;
+import jakarta.persistence.criteria.CriteriaQuery;
+import jakarta.persistence.criteria.Join;
+import jakarta.persistence.criteria.JoinType;
+import jakarta.persistence.criteria.Root;
+import jakarta.persistence.criteria.Subquery;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * @author Andreas Asplund
+ * @author Marco Belladelli
+ */
+@DomainModel( annotatedClasses = {
+		SubqueryMultipleLeftJoinsTest.MyUnrelatedEntity.class,
+		SubqueryMultipleLeftJoinsTest.MyEntity.class,
+		SubqueryMultipleLeftJoinsTest.AnotherEntity.class,
+		SubqueryMultipleLeftJoinsTest.AgainAnotherEntity.class
+} )
+@SessionFactory
+@Jira( "https://hibernate.atlassian.net/browse/HHH-16413" )
+public class SubqueryMultipleLeftJoinsTest {
+	private static final long ENTITY_WITH_ASSOCIATION_ID_1 = 1L;
+	private static final long ENTITY_WITH_ASSOCIATION_ID_2 = 2L;
+	private static final long ANOTHER_ENTITY_ID_1 = 3L;
+	private static final long ANOTHER_ENTITY_ID_2 = 4L;
+	private static final long AGAIN_ANOTHER_ENTITY_ID = 5L;
+
+	@BeforeAll
+	public void setUp(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final AgainAnotherEntity againAnotherEntity = new AgainAnotherEntity(
+					AGAIN_ANOTHER_ENTITY_ID,
+					"again"
+			);
+			session.persist( againAnotherEntity );
+			final AnotherEntity anotherEntity1 = new AnotherEntity(
+					ANOTHER_ENTITY_ID_1,
+					"another 1",
+					true,
+					null
+			);
+			session.persist( anotherEntity1 );
+			final AnotherEntity anotherEntity2 = new AnotherEntity(
+					ANOTHER_ENTITY_ID_2,
+					"another 2",
+					false,
+					againAnotherEntity
+			);
+			session.persist( anotherEntity2 );
+			session.persist( new MyEntity( ENTITY_WITH_ASSOCIATION_ID_1, "without association", anotherEntity1 ) );
+			session.persist( new MyEntity( ENTITY_WITH_ASSOCIATION_ID_2, "with association", anotherEntity2 ) );
+			session.persist( new MyUnrelatedEntity( ENTITY_WITH_ASSOCIATION_ID_1, "unrelated 1" ) );
+			session.persist( new MyUnrelatedEntity( ENTITY_WITH_ASSOCIATION_ID_2, "unrelated 2" ) );
+		} );
+	}
+
+	@AfterAll
+	public void tearDown(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			session.createMutationQuery( "delete from MyUnrelatedEntity" ).executeUpdate();
+			session.createMutationQuery( "delete from MyEntity" ).executeUpdate();
+			session.createMutationQuery( "delete from AnotherEntity" ).executeUpdate();
+			session.createMutationQuery( "delete from AgainAnotherEntity" ).executeUpdate();
+		} );
+	}
+
+	@Test
+	public void subqueryWithLeftJoinsCriteriaApi(SessionFactoryScope sessionFactoryScope) {
+		sessionFactoryScope.inTransaction( session -> {
+			final CriteriaBuilder cb = session.getCriteriaBuilder();
+			final CriteriaQuery<MyUnrelatedEntity> cq = cb.createQuery( MyUnrelatedEntity.class );
+			final Root<MyUnrelatedEntity> root = cq.from( MyUnrelatedEntity.class );
+			final Subquery<Long> subquery = cq.subquery( Long.class );
+			final Root<MyEntity> myEntityRoot = subquery.from( MyEntity.class );
+			final Join<MyEntity, AnotherEntity> anotherEntityJoin = myEntityRoot.join(
+					"otherEntity",
+					JoinType.LEFT
+			);
+			final Join<AnotherEntity, AgainAnotherEntity> againAnotherEntityJoin = anotherEntityJoin.join(
+					"otherEntity",
+					JoinType.LEFT
+			);
+			subquery.select( myEntityRoot.get( "id" ) ).where( cb.and(
+					cb.equal( anotherEntityJoin.get( "aString" ), "another 1" ),
+					cb.or(
+							cb.and(
+									cb.equal( anotherEntityJoin.get( "aBoolean" ), false ),
+									cb.equal( againAnotherEntityJoin.get( "aString" ), "again" )
+							),
+							cb.and(
+									// This should be true since "another 1" has no association and the join is LEFT
+									cb.equal( anotherEntityJoin.get( "aBoolean" ), true ),
+									cb.isNull( againAnotherEntityJoin.get( "aString" ) )
+							)
+					)
+			) );
+			final MyUnrelatedEntity result = session.createQuery(
+					cq.select( root ).where( root.get( "id" ).in( subquery ) )
+			).getSingleResult();
+			assertThat( result.getId() ).isEqualTo( 1L );
+			assertThat( result.getaString() ).isEqualTo( "unrelated 1" );
+		} );
+	}
+
+	@Entity( name = "MyUnrelatedEntity" )
+	public static class MyUnrelatedEntity {
+		@Id
+		private Long id;
+
+		private String aString;
+
+		public MyUnrelatedEntity() {
+		}
+
+		public MyUnrelatedEntity(Long id, String aString) {
+			this.id = id;
+			this.aString = aString;
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public String getaString() {
+			return aString;
+		}
+	}
+
+	@Entity( name = "MyEntity" )
+	public static class MyEntity {
+		@Id
+		private Long id;
+
+		private String aString;
+
+		@ManyToOne
+		private AnotherEntity otherEntity;
+
+		public MyEntity() {
+		}
+
+		public MyEntity(Long id, String aString, AnotherEntity otherEntity) {
+			this.id = id;
+			this.aString = aString;
+			this.otherEntity = otherEntity;
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public String getaString() {
+			return aString;
+		}
+
+		public AnotherEntity getOtherEntity() {
+			return otherEntity;
+		}
+	}
+
+	@Entity( name = "AnotherEntity" )
+	public static class AnotherEntity {
+		@Id
+		private Long id;
+
+		private String aString;
+
+		private boolean aBoolean;
+		@ManyToOne
+		private AgainAnotherEntity otherEntity;
+
+		public AnotherEntity() {
+		}
+
+		public AnotherEntity(Long id, String aString, boolean aBoolean, AgainAnotherEntity otherEntity) {
+			this.id = id;
+			this.aString = aString;
+			this.otherEntity = otherEntity;
+			this.aBoolean = aBoolean;
+		}
+
+		public String getaString() {
+			return aString;
+		}
+	}
+
+	@Entity( name = "AgainAnotherEntity" )
+	public static class AgainAnotherEntity {
+		@Id
+		private Long id;
+
+		private String aString;
+
+		@ManyToOne
+		private AnotherEntity otherEntity;
+
+		public AgainAnotherEntity() {
+		}
+
+		public AgainAnotherEntity(Long id, String aString) {
+			this.id = id;
+			this.aString = aString;
+		}
+	}
+}