diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/bytecode/enhancement/dirty/DynamicUpdateTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/bytecode/enhancement/dirty/DynamicUpdateTest.java
new file mode 100644
index 0000000000..da0ede6f82
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/bytecode/enhancement/dirty/DynamicUpdateTest.java
@@ -0,0 +1,178 @@
+package org.hibernate.orm.test.bytecode.enhancement.dirty;
+
+import java.math.BigDecimal;
+import java.time.LocalDate;
+
+import org.hibernate.annotations.DynamicUpdate;
+
+import org.hibernate.testing.bytecode.enhancement.BytecodeEnhancerRunner;
+import org.hibernate.testing.junit4.BaseCoreFunctionalTestCase;
+import org.hibernate.testing.orm.junit.JiraKey;
+import org.junit.Before;
+import org.junit.Test;
+import org.junit.runner.RunWith;
+
+import jakarta.persistence.CascadeType;
+import jakarta.persistence.Entity;
+import jakarta.persistence.FetchType;
+import jakarta.persistence.Id;
+import jakarta.persistence.OneToOne;
+
+import static org.assertj.core.api.AssertionsForClassTypes.assertThat;
+
+@RunWith(BytecodeEnhancerRunner.class)
+public class DynamicUpdateTest extends BaseCoreFunctionalTestCase {
+
+	public static final Long STUFF_TO_PAY_ID = 1l;
+	public static final Long PAYMENT_ID = 2l;
+
+	@Override
+	protected Class<?>[] getAnnotatedClasses() {
+		return new Class[] {
+				Payment.class,
+				StuffToPay.class
+		};
+	}
+
+	@Before
+	public void setUp() {
+		inTransaction(
+				session -> {
+					Payment payment = new Payment(PAYMENT_ID);
+					payment.setFee( new BigDecimal( 42 ) );
+					payment.setTransactionNumber( "1234567890" );
+
+					StuffToPay stuffToPay = new StuffToPay(STUFF_TO_PAY_ID);
+					stuffToPay.setPayment( payment );
+					session.persist( stuffToPay );
+				}
+		);
+	}
+
+	@Test
+	@JiraKey("HHH-16577")
+	public void testSetAttribute() {
+		inTransaction(
+				session -> {
+					StuffToPay stuffToPay = session.find( StuffToPay.class, STUFF_TO_PAY_ID );
+					stuffToPay.confirmPayment();
+					Payment payment = stuffToPay.getPayment();
+					payment.getTransactionNumber();
+					assertThat( payment.getPaidAt() ).isNotNull();				}
+		);
+
+		inTransaction(
+				session -> {
+					Payment payment = session.find( Payment.class, PAYMENT_ID );
+					assertThat(payment).isNotNull();
+					assertThat(payment.getPaidAt()).isNotNull();
+				}
+		);
+	}
+
+	@Entity
+	@DynamicUpdate
+	public static class Payment {
+
+		@Id
+		private Long id;
+
+		private BigDecimal fee;
+
+		private LocalDate paidAt;
+
+		private String transactionNumber;
+
+		public Payment() {
+		}
+
+		public Payment(Long id) {
+			this.id = id;
+		}
+
+		void confirmPayment(LocalDate when) {
+			this.paidAt = when;
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public BigDecimal getFee() {
+			return fee;
+		}
+
+		public void setFee(BigDecimal fee) {
+			this.fee = fee;
+		}
+
+		public LocalDate getPaidAt() {
+			return paidAt;
+		}
+
+		public void setPaidAt(LocalDate paidAt) {
+			this.paidAt = paidAt;
+		}
+
+		public String getTransactionNumber() {
+			return transactionNumber;
+		}
+
+		public void setTransactionNumber(String transactionNumber) {
+			this.transactionNumber = transactionNumber;
+		}
+	}
+
+	@Entity
+	@DynamicUpdate
+	public static class StuffToPay {
+
+		@Id
+		private Long id;
+
+		private String description;
+
+		@OneToOne(cascade = CascadeType.ALL, fetch = FetchType.LAZY, orphanRemoval = true)
+		private Payment payment;
+
+		public StuffToPay() {
+		}
+
+		public StuffToPay(Long id) {
+			this.id = id;
+		}
+
+		public void confirmPayment() {
+			payment.confirmPayment( LocalDate.now() );
+		}
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public Payment getPayment() {
+			return payment;
+		}
+
+		public void setPayment(Payment payment) {
+			this.payment = payment;
+		}
+
+		public String getDescription() {
+			return description;
+		}
+
+		public void setDescription(String description) {
+			this.description = description;
+		}
+	}
+
+}