diff --git a/hibernate-core/src/main/java/org/hibernate/boot/beanvalidation/BeanValidationEventListener.java b/hibernate-core/src/main/java/org/hibernate/boot/beanvalidation/BeanValidationEventListener.java
index 04bf58a0e805..42735bf68f4d 100644
--- a/hibernate-core/src/main/java/org/hibernate/boot/beanvalidation/BeanValidationEventListener.java
+++ b/hibernate-core/src/main/java/org/hibernate/boot/beanvalidation/BeanValidationEventListener.java
@@ -13,6 +13,7 @@
 import org.hibernate.boot.internal.ClassLoaderAccessImpl;
 import org.hibernate.boot.registry.classloading.spi.ClassLoaderService;
 import org.hibernate.engine.spi.SessionFactoryImplementor;
+import org.hibernate.engine.spi.SharedSessionContractImplementor;
 import org.hibernate.event.spi.PreCollectionUpdateEvent;
 import org.hibernate.event.spi.PreCollectionUpdateEventListener;
 import org.hibernate.event.spi.PreDeleteEvent;
@@ -51,8 +52,9 @@ public class BeanValidationEventListener
 	private final Validator validator;
 	private final GroupsPerOperation groupsPerOperation;
 
-	public BeanValidationEventListener(
-			ValidatorFactory factory, Map<String, Object> settings, ClassLoaderService classLoaderService) {
+	private SessionFactoryImplementor sessionFactory;
+
+	public BeanValidationEventListener(ValidatorFactory factory, Map<String, Object> settings, ClassLoaderService classLoaderService) {
 		traversableResolver = new HibernateTraversableResolver();
 		validator =
 				factory.usingContext()
@@ -63,9 +65,9 @@ public BeanValidationEventListener(
 
 	@Override
 	public void sessionFactoryCreated(SessionFactory factory) {
-		var implementor = factory.unwrap( SessionFactoryImplementor.class );
-		implementor.getMappingMetamodel()
-				.forEachEntityDescriptor( entityPersister -> traversableResolver.addPersister( entityPersister, implementor ) );
+		sessionFactory = factory.unwrap( SessionFactoryImplementor.class );
+		sessionFactory.getMappingMetamodel()
+				.forEachEntityDescriptor( entityPersister -> traversableResolver.addPersister( entityPersister, sessionFactory ) );
 	}
 
 	public boolean onPreInsert(PreInsertEvent event) {
@@ -110,11 +112,21 @@ public void onPreUpdateCollection(PreCollectionUpdateEvent event) {
 		final Object entity = castNonNull( event.getCollection().getOwner() );
 		validate(
 				entity,
-				event.getSession().getEntityPersister( event.getAffectedOwnerEntityName(), entity ),
+				getEntityPersister( event.getSession(), event.getAffectedOwnerEntityName(), entity ),
 				GroupsPerOperation.Operation.UPDATE
 		);
 	}
 
+	private EntityPersister getEntityPersister(SharedSessionContractImplementor session, String entityName, Object entity) {
+		if ( session != null ) {
+			return session.getEntityPersister( entityName, entity );
+		}
+		return entityName == null
+				? sessionFactory.getMappingMetamodel().getEntityDescriptor( entity.getClass().getName() )
+				: sessionFactory.getMappingMetamodel().getEntityDescriptor( entityName )
+						.getSubclassEntityPersister( entity, sessionFactory );
+	}
+
 	private <T> void validate(
 			T object,
 			EntityPersister persister,
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/annotations/beanvalidation/CollectionActionsValidationStatelessTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/annotations/beanvalidation/CollectionActionsValidationStatelessTest.java
new file mode 100644
index 000000000000..aff5004cd14d
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/annotations/beanvalidation/CollectionActionsValidationStatelessTest.java
@@ -0,0 +1,109 @@
+/*
+ * SPDX-License-Identifier: Apache-2.0
+ * Copyright Red Hat Inc. and Hibernate Authors
+ */
+package org.hibernate.orm.test.annotations.beanvalidation;
+
+import jakarta.persistence.Entity;
+import jakarta.persistence.Id;
+import jakarta.persistence.JoinColumn;
+import jakarta.persistence.ManyToOne;
+import jakarta.persistence.OneToMany;
+import jakarta.persistence.Table;
+import jakarta.validation.ConstraintViolationException;
+import jakarta.validation.constraints.Size;
+import org.hibernate.cfg.AvailableSettings;
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.Jira;
+import org.hibernate.testing.orm.junit.ServiceRegistry;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.hibernate.testing.orm.junit.Setting;
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.Test;
+
+import java.util.ArrayList;
+import java.util.List;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+@SessionFactory
+@DomainModel(annotatedClasses = {
+		CollectionActionsValidationStatelessTest.Author.class,
+		CollectionActionsValidationStatelessTest.Book.class,
+})
+@ServiceRegistry(settings = @Setting(name = AvailableSettings.JAKARTA_VALIDATION_MODE, value = "auto"))
+@Jira("https://hibernate.atlassian.net/browse/HHH-19843")
+public class CollectionActionsValidationStatelessTest {
+
+	@Test
+	void smoke(SessionFactoryScope scope) {
+		scope.inStatelessTransaction( session -> {
+			final ConstraintViolationException e = assertThrows( ConstraintViolationException.class, () -> {
+				ArrayList<Book> books = new ArrayList<>();
+				Author author = new Author( 1L, "first", "last", books );
+				Book book = new Book( 10L, "", author );
+				books.add( book );
+
+				session.upsertMultiple( List.of( author ) );
+			} );
+			assertThat( e.getConstraintViolations() ).hasSize( 1 );
+		} );
+	}
+
+	@AfterEach
+	public void tearDown(SessionFactoryScope scope) {
+		scope.getSessionFactory().getSchemaManager().truncate();
+	}
+
+	@Table(name = "author")
+	@Entity
+	static class Author {
+
+		public Author() {
+		}
+
+		public Author(long id, String firstName, String lastName, List<Book> books) {
+			this.firstName = firstName;
+			this.lastName = lastName;
+			this.books = books;
+			this.id = id;
+		}
+
+		@Id
+		Long id;
+
+		String firstName;
+
+		String lastName;
+
+		@OneToMany
+		@JoinColumn(name = "bookId")
+		@Size(min = 10)
+		List<Book> books;
+
+	}
+
+	@Table(name = "book")
+	@Entity
+	static class Book {
+
+		public Book() {
+		}
+
+		public Book(long id, String title, Author author) {
+			this.id = id;
+			this.title = title;
+			this.author = author;
+		}
+
+		@Id
+		Long id;
+
+		String title;
+
+		@ManyToOne
+		Author author;
+	}
+}