diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/annotations/id/IdClassAndAssociationsTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/annotations/id/IdClassAndAssociationsTest.java
new file mode 100644
index 0000000000..c3a4d42f1b
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/annotations/id/IdClassAndAssociationsTest.java
@@ -0,0 +1,230 @@
+package org.hibernate.orm.test.annotations.id;
+
+import java.io.Serializable;
+import java.util.HashSet;
+import java.util.List;
+import java.util.Set;
+
+import org.hibernate.testing.TestForIssue;
+import org.hibernate.testing.orm.junit.EntityManagerFactoryScope;
+import org.hibernate.testing.orm.junit.Jpa;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.CascadeType;
+import jakarta.persistence.Column;
+import jakarta.persistence.Entity;
+import jakarta.persistence.FetchType;
+import jakarta.persistence.GeneratedValue;
+import jakarta.persistence.GenerationType;
+import jakarta.persistence.Id;
+import jakarta.persistence.IdClass;
+import jakarta.persistence.JoinColumn;
+import jakarta.persistence.ManyToOne;
+import jakarta.persistence.OneToMany;
+import jakarta.persistence.Table;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+
+
+@Jpa(
+		annotatedClasses = {
+				IdClassAndAssociationsTest.CourseEnrollment.class,
+				IdClassAndAssociationsTest.Unit.class,
+				IdClassAndAssociationsTest.User.class,
+				IdClassAndAssociationsTest.UserRole.class
+		}
+)
+@TestForIssue( jiraKey = "HHH-16075")
+public class IdClassAndAssociationsTest {
+
+	@BeforeEach
+	public void setUp(EntityManagerFactoryScope scope) {
+		scope.inTransaction(
+				entityManager -> {
+					Unit unit = new Unit( "unit 1" );
+					User trainee = new User( "Roy", unit );
+
+					UserRole userRole = new UserRole( trainee, "Trainee" );
+
+					trainee.addUserRole( userRole );
+
+					CourseEnrollment courseEnrollment = new CourseEnrollment( 1l, trainee );
+
+					entityManager.persist( unit );
+					entityManager.persist( trainee );
+					entityManager.persist( userRole );
+
+					entityManager.persist( courseEnrollment );
+				}
+		);
+	}
+
+	@Test
+	public void testIt(EntityManagerFactoryScope scope) {
+		scope.inTransaction(
+				entityManager -> {
+					final List<CourseEnrollment> enrollments = entityManager.createQuery(
+									"SELECT c FROM CourseEnrollment c WHERE c.courseId = ?1 AND c.trainee.firstName like (?2)",
+									CourseEnrollment.class
+							)
+							.setParameter( 1, 1L )
+							.setParameter( 2, "Roy" )
+							.getResultList();
+
+					assertEquals( 1, enrollments.size() );
+
+					User trainer = enrollments.get( 0 ).getTrainee();
+					assertNotNull( trainer );
+					Set<UserRole> roles = trainer.getRoles();
+				}
+		);
+
+	}
+
+	@Entity(name = "CourseEnrollment")
+	@Table(name = "course_enrollment")
+	public static class CourseEnrollment {
+		@Id
+		@GeneratedValue(strategy = GenerationType.IDENTITY)
+		private Long id;
+
+		@Column(name = "course")
+		Long courseId;
+
+		@ManyToOne(fetch = FetchType.LAZY)
+		@JoinColumn(name = "trainee", referencedColumnName = "id")
+		User trainee;
+
+		public CourseEnrollment() {
+		}
+
+		public CourseEnrollment(Long courseId, User trainee) {
+			this.courseId = courseId;
+			this.trainee = trainee;
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public Long getCourseId() {
+			return courseId;
+		}
+
+		public User getTrainee() {
+			return trainee;
+		}
+
+	}
+
+	@Entity(name = "Unit")
+	@Table(name = "units")
+	public static class Unit {
+		@Id
+		@GeneratedValue(strategy = GenerationType.AUTO)
+		private Long id;
+
+		private String name;
+
+		public Unit() {
+		}
+
+		public Unit(String name) {
+			this.name = name;
+		}
+	}
+
+	@Entity(name = "User")
+	@Table(name = "users")
+	public static class User {
+		@Id
+		@GeneratedValue(strategy = GenerationType.AUTO)
+		private Long id;
+
+		@Column(name = "first_name")
+		private String firstName;
+
+		@ManyToOne
+		@JoinColumn(name = "unit")
+		private Unit unit;
+
+		@JoinColumn(name = "user_id", referencedColumnName = "id")
+		@OneToMany(fetch = FetchType.EAGER, orphanRemoval = true, cascade = CascadeType.ALL)
+		private Set<UserRole> roles = new HashSet<>();
+
+		public User() {
+		}
+
+		public User(String firstName, Unit unit) {
+			this.firstName = firstName;
+			this.unit = unit;
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public Set<UserRole> getRoles() {
+			return roles;
+		}
+
+		public void addUserRole(UserRole role) {
+			this.roles.add( role );
+		}
+	}
+
+	@Entity(name = "UserRole")
+	@Table(name = "users_roles")
+	@IdClass(UserRoleId.class)
+	public static class UserRole {
+
+		@Id
+		@ManyToOne
+		@JoinColumn(name = "user_id")
+		private User user;
+
+		@Id
+		@Column(name = "role_name")
+		private String roleName;
+
+		public UserRole() {
+		}
+
+		public UserRole(User user, String roleName) {
+			this.user = user;
+			this.roleName = roleName;
+		}
+	}
+
+	public static class UserRoleId implements Serializable {
+
+		private User user;
+		private String roleName;
+
+		public UserRoleId() {
+		}
+
+		public UserRoleId(User user, String roleName) {
+			this.user = user;
+			this.roleName = roleName;
+		}
+
+		public User getUser() {
+			return user;
+		}
+
+		public void setUser(User user) {
+			this.user = user;
+		}
+
+		public String getRoleName() {
+			return roleName;
+		}
+
+		public void setRoleName(String roleName) {
+			this.roleName = roleName;
+		}
+	}
+}