diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/schematools/EnumCheckColumnDefinitionTests.java b/hibernate-core/src/test/java/org/hibernate/orm/test/schematools/EnumCheckColumnDefinitionTests.java
new file mode 100644
index 0000000000..ade5ea8557
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/schematools/EnumCheckColumnDefinitionTests.java
@@ -0,0 +1,173 @@
+/*
+ * 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.schematools;
+
+import java.lang.annotation.RetentionPolicy;
+import java.util.ArrayList;
+import java.util.EnumSet;
+import java.util.List;
+import java.util.Map;
+
+import org.hibernate.boot.Metadata;
+import org.hibernate.boot.MetadataSources;
+import org.hibernate.boot.registry.StandardServiceRegistry;
+import org.hibernate.boot.registry.StandardServiceRegistryBuilder;
+import org.hibernate.cfg.AvailableSettings;
+import org.hibernate.dialect.Dialect;
+import org.hibernate.dialect.MySQLDialect;
+import org.hibernate.engine.config.spi.ConfigurationService;
+import org.hibernate.orm.test.tool.schema.ExecutionOptionsTestImpl;
+import org.hibernate.service.spi.ServiceRegistryImplementor;
+import org.hibernate.tool.schema.SourceType;
+import org.hibernate.tool.schema.TargetType;
+import org.hibernate.tool.schema.internal.HibernateSchemaManagementTool;
+import org.hibernate.tool.schema.internal.exec.GenerationTarget;
+import org.hibernate.tool.schema.internal.exec.JdbcContext;
+import org.hibernate.tool.schema.spi.SchemaCreator;
+import org.hibernate.tool.schema.spi.SchemaManagementTool;
+import org.hibernate.tool.schema.spi.ScriptSourceInput;
+import org.hibernate.tool.schema.spi.ScriptTargetOutput;
+import org.hibernate.tool.schema.spi.SourceDescriptor;
+import org.hibernate.tool.schema.spi.TargetDescriptor;
+import org.hibernate.type.NumericBooleanConverter;
+import org.hibernate.type.YesNoConverter;
+
+import org.hibernate.testing.orm.junit.JiraKey;
+import org.hibernate.testing.orm.junit.ServiceRegistryScope;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.Basic;
+import jakarta.persistence.Column;
+import jakarta.persistence.Convert;
+import jakarta.persistence.Entity;
+import jakarta.persistence.EnumType;
+import jakarta.persistence.Enumerated;
+import jakarta.persistence.Id;
+import jakarta.persistence.Table;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+@JiraKey("HHH-16670")
+public class EnumCheckColumnDefinitionTests {
+	@Test
+	public void testFallbackToolIsPickedUp() {
+		ServiceRegistryScope.using(
+				() -> {
+					return new StandardServiceRegistryBuilder()
+							.applySetting( AvailableSettings.DIALECT, CustomDialect.class.getName() )
+							.build();
+				},
+				(registryScope) ->  {
+					final StandardServiceRegistry registry = registryScope.getRegistry();
+					final Metadata metadata = new MetadataSources( registry )
+							.addAnnotatedClass( SimpleEntity.class )
+							.buildMetadata();
+
+					final HibernateSchemaManagementTool tool = (HibernateSchemaManagementTool) registry.getService( SchemaManagementTool.class );
+					final Map<String, Object> settings = registry.getService( ConfigurationService.class ).getSettings();
+					final SchemaCreator schemaCreator = tool.getSchemaCreator( settings );
+					schemaCreator.doCreation(
+							metadata,
+							new ExecutionOptionsTestImpl(),
+							contributed -> true,
+							new SourceDescriptor() {
+								@Override
+								public SourceType getSourceType() {
+									return SourceType.METADATA;
+								}
+
+								@Override
+								public ScriptSourceInput getScriptSourceInput() {
+									return null;
+								}
+							},
+							new TargetDescriptor() {
+								@Override
+								public EnumSet<TargetType> getTargetTypes() {
+									return EnumSet.of( TargetType.DATABASE );
+								}
+
+								@Override
+								public ScriptTargetOutput getScriptTargetOutput() {
+									return null;
+								}
+							}
+					);
+
+					assertThat( CollectingGenerationTarget.commands.get( 0) ).contains( "enum ('SOURCE','CLASS','RUNTIME')");
+				}
+		);
+	}
+
+	private static class CollectingGenerationTarget implements GenerationTarget {
+		public static final List<String> commands = new ArrayList<>();
+
+		public CollectingGenerationTarget(JdbcContext jdbcContext, boolean needsAutoCommit) {
+		}
+
+		@Override
+		public void prepare() {
+			commands.clear();
+		}
+
+		@Override
+		public void accept(String command) {
+			commands.add( command );
+		}
+
+		@Override
+		public void release() {
+		}
+	}
+
+	public static class SchemaManagementToolImpl extends HibernateSchemaManagementTool {
+		@Override
+		protected GenerationTarget buildDatabaseTarget(JdbcContext jdbcContext, boolean needsAutoCommit) {
+			return new CollectingGenerationTarget( jdbcContext, needsAutoCommit );
+		}
+	}
+
+	public static class CustomDialect extends MySQLDialect {
+		@Override
+		public SchemaManagementTool getFallbackSchemaManagementTool(Map<String, Object> configurationValues, ServiceRegistryImplementor registry) {
+			return new SchemaManagementToolImpl();
+		}
+	}
+
+	@Entity( name = "SimpleEntity" )
+	@Table( name = "SimpleEntity" )
+	public static class SimpleEntity {
+	    @Id
+	    private Integer id;
+	    @Basic
+		private String name;
+		@Column(columnDefinition = "enum ('SOURCE','CLASS','RUNTIME')")
+		@Enumerated(EnumType.STRING)
+		RetentionPolicy retentionPolicy;
+
+		private SimpleEntity() {
+			// for use by Hibernate
+		}
+
+		public SimpleEntity(Integer id, String name) {
+			this.id = id;
+			this.name = name;
+		}
+
+		public Integer getId() {
+			return id;
+		}
+
+		public String getName() {
+			return name;
+		}
+
+		public void setName(String name) {
+			this.name = name;
+		}
+	}
+}