diff --git a/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java b/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java
index d140524d8bd0..632acc93be34 100644
--- a/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java
+++ b/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java
@@ -7664,14 +7664,17 @@ else if ( !dialect.supportsRowValueConstructorSyntaxInInList() ) {
 					appendSql( CLOSE_PARENTHESIS );
 				}
 				else {
-					String separator = NO_SEPARATOR;
+					if (inListPredicate.isNegated()) {
+						appendSql("not ");
+					}
 					appendSql( OPEN_PARENTHESIS );
-					for ( Expression expression : listExpressions ) {
-						appendSql( separator );
+					String separator = NO_SEPARATOR;
+					for (Expression expression : listExpressions) {
+						appendSql(separator);
 						emulateTupleComparison(
 								lhsTuple.getExpressions(),
-								getSqlTuple( expression ).getExpressions(),
-								comparisonOperator,
+								SqlTupleContainer.getSqlTuple(expression).getExpressions(),
+								ComparisonOperator.EQUAL,
 								true
 						);
 						separator = " or ";
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/Foo.java b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/Foo.java
new file mode 100644
index 000000000000..60174b52b959
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/Foo.java
@@ -0,0 +1,55 @@
+/*
+ * SPDX-License-Identifier: Apache-2.0
+ * Copyright Red Hat Inc. and Hibernate Authors
+ */
+package org.hibernate.orm.test.jpa.criteria.basic;
+import jakarta.persistence.Entity;
+import jakarta.persistence.Id;
+import jakarta.persistence.JoinColumn;
+import jakarta.persistence.JoinColumns;
+import jakarta.persistence.ManyToOne;
+
+import java.util.Objects;
+
+/**
+ * Entity used in <code>org.hibernate.orm.test.jpa.criteria.basic.NegatedInPredicateTest</code>.
+ *
+ * @author Mike Mannion
+ */
+@Entity
+public class Foo {
+
+	@Id
+	Long id;
+
+	@ManyToOne
+	@JoinColumns({
+			@JoinColumn(name = "FK_CODE", referencedColumnName = "CODE"),
+			@JoinColumn(name = "FK_CONTEXT", referencedColumnName = "CONTEXT")
+	})
+	FooType fooType;
+
+	public Foo() {
+		// For JPA
+	}
+
+	public Foo(Long id, FooType fooType) {
+		this.id = id;
+		this.fooType = fooType;
+	}
+
+	@Override
+	public boolean equals(Object o) {
+		if (o == null || getClass() != o.getClass()) return false;
+
+		Foo customer = (Foo) o;
+		return Objects.equals(id, customer.id) && Objects.equals(fooType, customer.fooType);
+	}
+
+	@Override
+	public int hashCode() {
+		int result = Objects.hashCode(id);
+		result = 31 * result + Objects.hashCode(fooType);
+		return result;
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/FooType.java b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/FooType.java
new file mode 100644
index 000000000000..991732ec458f
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/FooType.java
@@ -0,0 +1,32 @@
+/*
+ * SPDX-License-Identifier: Apache-2.0
+ * Copyright Red Hat Inc. and Hibernate Authors
+ */
+package org.hibernate.orm.test.jpa.criteria.basic;
+import jakarta.persistence.Column;
+import jakarta.persistence.Entity;
+import jakarta.persistence.Id;
+
+/**
+ * Entity used in <code>org.hibernate.orm.test.jpa.criteria.basic.NegatedInPredicateTest</code>.
+ *
+ * @author Mike Mannion
+ */
+@Entity
+public class FooType {
+	@Id
+	@Column(name = "CODE")
+	String code;
+
+	@Column(name = "CONTEXT")
+	String context;
+
+	public FooType() {
+		// For JPA
+	}
+
+	FooType(String code, String context) {
+		this.code = code;
+		this.context = context;
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/NegatedInPredicateTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/NegatedInPredicateTest.java
new file mode 100644
index 000000000000..e1d4a2bc3f23
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/jpa/criteria/basic/NegatedInPredicateTest.java
@@ -0,0 +1,111 @@
+/*
+ * SPDX-License-Identifier: Apache-2.0
+ * Copyright Red Hat Inc. and Hibernate Authors
+ */
+package org.hibernate.orm.test.jpa.criteria.basic;
+
+import jakarta.persistence.criteria.CriteriaBuilder;
+import jakarta.persistence.criteria.CriteriaQuery;
+import jakarta.persistence.criteria.Root;
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.JiraKey;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+
+import java.util.List;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+
+/**
+ * Add test which composes not with in. Test introduced after discovery the negated in
+ * fails under dialects without record-level construction, such as DB2.
+ *
+ * @author Mike Mannion
+ */
+@JiraKey(value = "HHH-19497")
+@DomainModel(
+		annotatedClasses = {Foo.class, FooType.class}
+)
+@SessionFactory
+class NegatedInPredicateTest {
+
+	public static final FooType FOO_TYPE1 = new FooType( "ft1", "ctx1" );
+	public static final FooType FOO_TYPE2 = new FooType( "ft2", "ctx1" );
+
+	@BeforeEach
+	void setup(SessionFactoryScope scope) {
+		scope.inTransaction(
+				em -> {
+					em.persist( FOO_TYPE1 );
+					em.persist( FOO_TYPE2 );
+
+					Foo foo1 = new Foo( 1L, FOO_TYPE1 );
+					Foo foo2 = new Foo( 2L, FOO_TYPE1 );
+					Foo foo3 = new Foo( 3L, FOO_TYPE2 );
+
+					em.persist( foo1 );
+					em.persist( foo2 );
+					em.persist( foo3 );
+				}
+		);
+	}
+
+	@AfterEach
+	void tearDown(SessionFactoryScope scope) {
+		scope.inTransaction(
+				em -> {
+					em.createQuery( "delete from Foo" ).executeUpdate();
+					em.createQuery( "delete from FooType" ).executeUpdate();
+				}
+		);
+	}
+
+	@Test
+	void testSanity(SessionFactoryScope scope) {
+		scope.inTransaction(
+				em -> {
+					CriteriaBuilder cb = em.getCriteriaBuilder();
+					CriteriaQuery<Foo> cq = cb.createQuery( Foo.class );
+					Root<Foo> root = cq.from( Foo.class );
+					assertThat( em.createQuery( cq.select( root ) ).getResultList() )
+							.hasSize( 3 );
+				}
+		);
+	}
+
+	@Test
+	void testNegatedPredicate(SessionFactoryScope scope) {
+		scope.inTransaction(
+				em -> {
+					CriteriaBuilder cb = em.getCriteriaBuilder();
+					CriteriaQuery<Foo> cq = cb.createQuery( Foo.class );
+					Root<Foo> root = cq.from( Foo.class );
+					cq.select( root )
+							.where( cb.not( root.get( "fooType" ).in( List.of( FOO_TYPE1, FOO_TYPE2 ) ) ) );
+					assertThat( em.createQuery( cq ).getResultList() )
+							.isEmpty();
+				}
+		);
+	}
+
+	@Test
+	void testNonNegatedInPredicate(SessionFactoryScope scope) {
+		scope.inTransaction(
+				em -> {
+					CriteriaBuilder cb = em.getCriteriaBuilder();
+					CriteriaQuery<Foo> cq = cb.createQuery( Foo.class );
+					Root<Foo> root = cq.from( Foo.class );
+					cq.select( root )
+							.where( root.get( "fooType" ).in( List.of( FOO_TYPE1, FOO_TYPE2 ) ) );
+					assertThat( em.createQuery( cq ).getResultList() )
+							.hasSize( 3 );
+
+				}
+		);
+	}
+
+}