diff --git a/spring-boot-project/spring-boot-devtools/pom.xml b/spring-boot-project/spring-boot-devtools/pom.xml
index 01ba6dfa1d..3f683bc32a 100644
--- a/spring-boot-project/spring-boot-devtools/pom.xml
+++ b/spring-boot-project/spring-boot-devtools/pom.xml
@@ -29,6 +29,11 @@
 			<artifactId>javax.servlet-api</artifactId>
 			<optional>true</optional>
 		</dependency>
+		<dependency>
+			<groupId>org.apache.derby</groupId>
+			<artifactId>derby</artifactId>
+			<optional>true</optional>
+		</dependency>
 		<dependency>
 			<groupId>org.springframework</groupId>
 			<artifactId>spring-jdbc</artifactId>
@@ -121,11 +126,6 @@
 			<artifactId>spring-hateoas</artifactId>
 			<scope>test</scope>
 		</dependency>
-		<dependency>
-			<groupId>org.apache.derby</groupId>
-			<artifactId>derby</artifactId>
-			<scope>test</scope>
-		</dependency>
 		<dependency>
 			<groupId>org.apache.derby</groupId>
 			<artifactId>derbyclient</artifactId>
diff --git a/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/DevToolsDataSourceAutoConfiguration.java b/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/DevToolsDataSourceAutoConfiguration.java
index c9bf441c24..7780be5bd6 100644
--- a/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/DevToolsDataSourceAutoConfiguration.java
+++ b/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/DevToolsDataSourceAutoConfiguration.java
@@ -17,13 +17,17 @@
 package org.springframework.boot.devtools.autoconfigure;
 
 import java.sql.Connection;
+import java.sql.SQLException;
 import java.sql.Statement;
 import java.util.Arrays;
 import java.util.HashSet;
+import java.util.Properties;
 import java.util.Set;
 
 import javax.sql.DataSource;
 
+import org.apache.derby.jdbc.EmbeddedDriver;
+
 import org.springframework.beans.factory.DisposableBean;
 import org.springframework.beans.factory.annotation.AnnotatedBeanDefinition;
 import org.springframework.beans.factory.config.BeanDefinition;
@@ -94,40 +98,53 @@ public class DevToolsDataSourceAutoConfiguration {
 
 		@Override
 		public void destroy() throws Exception {
-			if (dataSourceRequiresShutdown()) {
-				try (Connection connection = this.dataSource.getConnection()) {
-					try (Statement statement = connection.createStatement()) {
-						statement.execute("SHUTDOWN");
-					}
-				}
-			}
-		}
-
-		private boolean dataSourceRequiresShutdown() {
 			for (InMemoryDatabase inMemoryDatabase : InMemoryDatabase.values()) {
 				if (inMemoryDatabase.matches(this.dataSourceProperties)) {
-					return true;
+					inMemoryDatabase.shutdown(this.dataSource);
+					return;
 				}
 			}
-			return false;
 		}
 
 		private enum InMemoryDatabase {
 
-			DERBY(null, "org.apache.derby.jdbc.EmbeddedDriver"),
+			DERBY(null, new HashSet<>(Arrays.asList("org.apache.derby.jdbc.EmbeddedDriver")), (dataSource) -> {
+				String url = dataSource.getConnection().getMetaData().getURL();
+				try {
+					new EmbeddedDriver().connect(url + ";drop=true", new Properties());
+				}
+				catch (SQLException ex) {
+					if (!"08006".equals(ex.getSQLState())) {
+						throw ex;
+					}
+				}
+			}),
 
-			H2("jdbc:h2:mem:", "org.h2.Driver", "org.h2.jdbcx.JdbcDataSource"),
+			H2("jdbc:h2:mem:", new HashSet<>(Arrays.asList("org.h2.Driver", "org.h2.jdbcx.JdbcDataSource"))),
 
-			HSQLDB("jdbc:hsqldb:mem:", "org.hsqldb.jdbcDriver", "org.hsqldb.jdbc.JDBCDriver",
-					"org.hsqldb.jdbc.pool.JDBCXADataSource");
+			HSQLDB("jdbc:hsqldb:mem:", new HashSet<>(Arrays.asList("org.hsqldb.jdbcDriver",
+					"org.hsqldb.jdbc.JDBCDriver", "org.hsqldb.jdbc.pool.JDBCXADataSource")));
 
 			private final String urlPrefix;
 
+			private final ShutdownHandler shutdownHandler;
+
 			private final Set<String> driverClassNames;
 
-			InMemoryDatabase(String urlPrefix, String... driverClassNames) {
+			InMemoryDatabase(String urlPrefix, Set<String> driverClassNames) {
+				this(urlPrefix, driverClassNames, (dataSource) -> {
+					try (Connection connection = dataSource.getConnection()) {
+						try (Statement statement = connection.createStatement()) {
+							statement.execute("SHUTDOWN");
+						}
+					}
+				});
+			}
+
+			InMemoryDatabase(String urlPrefix, Set<String> driverClassNames, ShutdownHandler shutdownHandler) {
 				this.urlPrefix = urlPrefix;
-				this.driverClassNames = new HashSet<>(Arrays.asList(driverClassNames));
+				this.driverClassNames = driverClassNames;
+				this.shutdownHandler = shutdownHandler;
 			}
 
 			boolean matches(DataSourceProperties properties) {
@@ -136,6 +153,17 @@ public class DevToolsDataSourceAutoConfiguration {
 						&& this.driverClassNames.contains(properties.determineDriverClassName());
 			}
 
+			void shutdown(DataSource dataSource) throws SQLException {
+				this.shutdownHandler.shutdown(dataSource);
+			}
+
+			@FunctionalInterface
+			interface ShutdownHandler {
+
+				void shutdown(DataSource dataSource) throws SQLException;
+
+			}
+
 		}
 
 	}
diff --git a/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/DevToolsPooledDataSourceAutoConfigurationTests.java b/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/DevToolsPooledDataSourceAutoConfigurationTests.java
index ea5b5e287e..5e3dee05c6 100644
--- a/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/DevToolsPooledDataSourceAutoConfigurationTests.java
+++ b/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/DevToolsPooledDataSourceAutoConfigurationTests.java
@@ -18,16 +18,21 @@ package org.springframework.boot.devtools.autoconfigure;
 
 import java.sql.SQLException;
 import java.sql.Statement;
+import java.util.Properties;
 
 import javax.sql.DataSource;
 
+import org.apache.derby.jdbc.EmbeddedDriver;
 import org.junit.After;
 import org.junit.Before;
 import org.junit.Test;
 
 import org.springframework.boot.autoconfigure.jdbc.DataSourceAutoConfiguration;
 import org.springframework.context.ConfigurableApplicationContext;
+import org.springframework.jdbc.core.JdbcTemplate;
 
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
 import static org.mockito.Mockito.never;
 import static org.mockito.Mockito.times;
 import static org.mockito.Mockito.verify;
@@ -115,10 +120,15 @@ public class DevToolsPooledDataSourceAutoConfigurationTests extends AbstractDevT
 	@Test
 	public void inMemoryDerbyIsShutdown() throws SQLException {
 		ConfigurableApplicationContext context = createContext("org.apache.derby.jdbc.EmbeddedDriver",
-				"jdbc:derby:memory:test", DataSourceAutoConfiguration.class, DataSourceSpyConfiguration.class);
-		Statement statement = configureDataSourceBehavior(context.getBean(DataSource.class));
+				"jdbc:derby:memory:test;create=true", DataSourceAutoConfiguration.class,
+				DataSourceSpyConfiguration.class);
+		JdbcTemplate jdbc = new JdbcTemplate(context.getBean(DataSource.class));
+		jdbc.execute("SELECT 1 FROM SYSIBM.SYSDUMMY1");
 		context.close();
-		verify(statement, times(1)).execute("SHUTDOWN");
+		// Connect should fail as DB no longer exists
+		assertThatExceptionOfType(SQLException.class)
+				.isThrownBy(() -> new EmbeddedDriver().connect("jdbc:derby:memory:test", new Properties()))
+				.satisfies((ex) -> assertThat(ex.getSQLState()).isEqualTo("XJ004"));
 	}
 
 }