diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/any/annotations/AnyNullabilityTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/any/annotations/AnyNullabilityTest.java
new file mode 100644
index 0000000000..0e8c7640bd
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/any/annotations/AnyNullabilityTest.java
@@ -0,0 +1,264 @@
+/*
+ * 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.any.annotations;
+
+import org.hibernate.PropertyValueException;
+import org.hibernate.annotations.Any;
+import org.hibernate.annotations.AnyDiscriminator;
+import org.hibernate.annotations.AnyDiscriminatorValue;
+import org.hibernate.annotations.AnyKeyJavaClass;
+
+import org.hibernate.testing.orm.junit.DomainModel;
+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.Test;
+
+import jakarta.persistence.Column;
+import jakarta.persistence.DiscriminatorType;
+import jakarta.persistence.Entity;
+import jakarta.persistence.Id;
+import jakarta.persistence.JoinColumn;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.junit.jupiter.api.Assertions.fail;
+
+/**
+ * @author Marco Belladelli
+ */
+@DomainModel( annotatedClasses = {
+		AnyNullabilityTest.IntegerProperty.class,
+		AnyNullabilityTest.StringProperty.class,
+		AnyNullabilityTest.OptionalPropertyHolder.class,
+		AnyNullabilityTest.NonOptionalPropertyHolder.class,
+		AnyNullabilityTest.NonNullablePropertyHolder.class,
+} )
+@SessionFactory
+public class AnyNullabilityTest {
+	@AfterAll
+	public void tearDown(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			session.createMutationQuery( "delete from OptionalPropertyHolder" ).executeUpdate();
+		} );
+	}
+
+	@Test
+	public void testOptionalAny(SessionFactoryScope scope) {
+		scope.inTransaction( session -> {
+			final OptionalPropertyHolder emptyPropertyHolder = new OptionalPropertyHolder();
+			emptyPropertyHolder.setId( 1L );
+			session.persist( emptyPropertyHolder );
+		} );
+		scope.inTransaction( session -> {
+			final OptionalPropertyHolder propertyHolder = session.find( OptionalPropertyHolder.class, 1L );
+			assertThat( propertyHolder.getProperty() ).isNull();
+		} );
+	}
+
+	@Test
+	public void testNonOptionalAny(SessionFactoryScope scope) {
+		try {
+			scope.inTransaction( session -> {
+				final NonOptionalPropertyHolder emptyPropertyHolder = new NonOptionalPropertyHolder();
+				emptyPropertyHolder.setId( 2L );
+				session.persist( emptyPropertyHolder );
+			} );
+			fail( "Non-optional any was persisted with a non-valid `null` value" );
+		}
+		catch (Exception e) {
+			assertThat( e ).isInstanceOf( PropertyValueException.class );
+			assertThat( e.getMessage() ).contains( "not-null property references a null or transient value" );
+		}
+	}
+
+	@Test
+	public void testOptionalAnyNonNullable(SessionFactoryScope scope) {
+		try {
+			scope.inTransaction( session -> {
+				final NonNullablePropertyHolder emptyPropertyHolder = new NonNullablePropertyHolder();
+				emptyPropertyHolder.setId( 3L );
+				session.persist( emptyPropertyHolder );
+			} );
+			fail( "Non-optional any was persisted with a non-valid `null` value" );
+		}
+		catch (Exception e) {
+			assertThat( e ).isInstanceOf( PropertyValueException.class );
+			assertThat( e.getMessage() ).contains( "not-null property references a null or transient value" );
+		}
+	}
+
+	public interface Property<T> {
+		String getName();
+
+		T getValue();
+	}
+
+	@Entity( name = "IntegerProperty" )
+	public static class IntegerProperty implements Property<Integer> {
+		@Id
+		private Long id;
+
+		private String name;
+
+		private Integer value;
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		@Override
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+
+		@Override
+		public Integer getValue() {
+			return value;
+		}
+
+		public void setValue(Integer value) {
+			this.value = value;
+		}
+	}
+
+	@Entity( name = "StringProperty" )
+	public static class StringProperty implements Property<String> {
+		@Id
+		private Long id;
+
+		private String name;
+
+		private String value;
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		@Override
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+
+		@Override
+		public String getValue() {
+			return value;
+		}
+
+		public void setValue(String value) {
+			this.value = value;
+		}
+	}
+
+	@Entity( name = "OptionalPropertyHolder" )
+	public static class OptionalPropertyHolder {
+		@Id
+		private Long id;
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public Property<?> getProperty() {
+			return property;
+		}
+
+		public void setProperty(Property<?> property) {
+			this.property = property;
+		}
+
+		@Any
+		@AnyDiscriminator( DiscriminatorType.STRING )
+		@AnyDiscriminatorValue( discriminator = "S", entity = StringProperty.class )
+		@AnyDiscriminatorValue( discriminator = "I", entity = IntegerProperty.class )
+		@AnyKeyJavaClass( Long.class )
+		@Column( name = "property_type" )
+		@JoinColumn( name = "property_id" )
+		private Property<?> property;
+	}
+
+	@Entity( name = "NonOptionalPropertyHolder" )
+	public static class NonOptionalPropertyHolder {
+		@Id
+		private Long id;
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public Property<?> getProperty() {
+			return property;
+		}
+
+		public void setProperty(Property<?> property) {
+			this.property = property;
+		}
+
+		@Any( optional = false )
+		@AnyDiscriminator( DiscriminatorType.STRING )
+		@AnyDiscriminatorValue( discriminator = "S", entity = StringProperty.class )
+		@AnyDiscriminatorValue( discriminator = "I", entity = IntegerProperty.class )
+		@AnyKeyJavaClass( Long.class )
+		@Column( name = "property_type" )
+		@JoinColumn( name = "property_id" )
+		private Property<?> property;
+	}
+
+	@Entity( name = "NonNullablePropertyHolder" )
+	public static class NonNullablePropertyHolder {
+		@Id
+		private Long id;
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public Property<?> getProperty() {
+			return property;
+		}
+
+		public void setProperty(Property<?> property) {
+			this.property = property;
+		}
+
+		@Any( optional = true )
+		@AnyDiscriminator( DiscriminatorType.STRING )
+		@AnyDiscriminatorValue( discriminator = "S", entity = StringProperty.class )
+		@AnyDiscriminatorValue( discriminator = "I", entity = IntegerProperty.class )
+		@AnyKeyJavaClass( Long.class )
+		@Column( name = "property_type" )
+		@JoinColumn( name = "property_id", nullable = false )
+		private Property<?> property;
+	}
+}