diff --git a/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsGradleBuildCustomizer.java b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsGradleBuildCustomizer.java
new file mode 100644
index 00000000..1ea367ce
--- /dev/null
+++ b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsGradleBuildCustomizer.java
@@ -0,0 +1,67 @@
+/*
+ * Copyright 2012-2020 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package io.spring.initializr.generator.spring.dependency.devtools;
+
+import io.spring.initializr.generator.buildsystem.Dependency;
+import io.spring.initializr.generator.buildsystem.gradle.GradleBuild;
+import io.spring.initializr.generator.buildsystem.gradle.GradleDependency;
+import io.spring.initializr.generator.spring.build.BuildCustomizer;
+import io.spring.initializr.generator.version.Version;
+import io.spring.initializr.generator.version.VersionParser;
+import io.spring.initializr.generator.version.VersionRange;
+
+/**
+ * Gradle {@link BuildCustomizer} that creates a dedicated "developmentOnly" configuration
+ * when devtools is selected.
+ *
+ * @author Stephane Nicoll
+ */
+public class DevToolsGradleBuildCustomizer implements BuildCustomizer<GradleBuild> {
+
+	private static final VersionRange SPRING_BOOT_2_3_0_RC1_OR_LATER = VersionParser.DEFAULT.parseRange("2.3.0.RC1");
+
+	private final Version platformVersion;
+
+	private final String devtoolsDependencyId;
+
+	/**
+	 * Create a new instance with the requested {@link Version platform version} and the
+	 * identifier for the devtools dependency.
+	 * @param platformVersion the version of the plateform
+	 * @param devtoolsDependencyId the id of the devtools dependency
+	 */
+	public DevToolsGradleBuildCustomizer(Version platformVersion, String devtoolsDependencyId) {
+		this.platformVersion = platformVersion;
+		this.devtoolsDependencyId = devtoolsDependencyId;
+	}
+
+	@Override
+	public void customize(GradleBuild build) {
+		Dependency devtools = build.dependencies().get(this.devtoolsDependencyId);
+		if (devtools == null) {
+			return;
+		}
+		if (!SPRING_BOOT_2_3_0_RC1_OR_LATER.match(this.platformVersion)) {
+			build.configurations().add("developmentOnly");
+			build.configurations().customize("runtimeClasspath",
+					(runtimeClasspath) -> runtimeClasspath.extendsFrom("developmentOnly"));
+		}
+		build.dependencies().add(this.devtoolsDependencyId,
+				GradleDependency.from(devtools).configuration("developmentOnly"));
+	}
+
+}
diff --git a/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsMavenBuildCustomizer.java b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsMavenBuildCustomizer.java
new file mode 100644
index 00000000..50b52199
--- /dev/null
+++ b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsMavenBuildCustomizer.java
@@ -0,0 +1,49 @@
+/*
+ * Copyright 2012-2019 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package io.spring.initializr.generator.spring.dependency.devtools;
+
+import io.spring.initializr.generator.buildsystem.Dependency;
+import io.spring.initializr.generator.buildsystem.maven.MavenBuild;
+import io.spring.initializr.generator.buildsystem.maven.MavenDependency;
+import io.spring.initializr.generator.spring.build.BuildCustomizer;
+
+/**
+ * Maven {@link BuildCustomizer} that sets the "optional" flag when devtools is selected.
+ *
+ * @author Stephane Nicoll
+ */
+public class DevToolsMavenBuildCustomizer implements BuildCustomizer<MavenBuild> {
+
+	private final String devtoolsDependencyId;
+
+	/**
+	 * Create a new instance with the identifier for the devtools dependency.
+	 * @param devtoolsDependencyId the id of the devtools dependency
+	 */
+	public DevToolsMavenBuildCustomizer(String devtoolsDependencyId) {
+		this.devtoolsDependencyId = devtoolsDependencyId;
+	}
+
+	@Override
+	public void customize(MavenBuild build) {
+		Dependency devtools = build.dependencies().get(this.devtoolsDependencyId);
+		if (devtools != null) {
+			build.dependencies().add("devtools", MavenDependency.from(devtools).optional(true));
+		}
+	}
+
+}
diff --git a/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/package-info.java b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/package-info.java
new file mode 100644
index 00000000..0d8bcd75
--- /dev/null
+++ b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/dependency/devtools/package-info.java
@@ -0,0 +1,20 @@
+/*
+ * Copyright 2012-2020 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+/**
+ * Customizations for Spring Boot DevTools.
+ */
+package io.spring.initializr.generator.spring.dependency.devtools;
diff --git a/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsGradleBuildCustomizerTests.java b/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsGradleBuildCustomizerTests.java
new file mode 100644
index 00000000..29461a7a
--- /dev/null
+++ b/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsGradleBuildCustomizerTests.java
@@ -0,0 +1,74 @@
+/*
+ * Copyright 2012-2020 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package io.spring.initializr.generator.spring.dependency.devtools;
+
+import io.spring.initializr.generator.buildsystem.Dependency;
+import io.spring.initializr.generator.buildsystem.gradle.GradleBuild;
+import io.spring.initializr.generator.buildsystem.gradle.GradleDependency;
+import io.spring.initializr.generator.version.Version;
+import org.junit.jupiter.api.Test;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.mockito.Mockito.mock;
+
+/**
+ * Tests for {@link DevToolsGradleBuildCustomizer}.
+ *
+ * @author Stephane Nicoll
+ */
+class DevToolsGradleBuildCustomizerTests {
+
+	private static final Dependency DEVTOOLS_DEPENDENCY = Dependency
+			.withCoordinates("org.springframework.boot", "spring-boot-devtools").build();
+
+	@Test
+	void gradleWithDevtoolsAndSpringBootPriorTo23RC1CreatesDevelopmentOnlyConfiguration() {
+		GradleBuild build = new GradleBuild();
+		build.dependencies().add("devtools", DEVTOOLS_DEPENDENCY);
+		new DevToolsGradleBuildCustomizer(Version.parse("2.3.0.M4"), "devtools").customize(build);
+		assertThat(build.configurations().names()).containsOnly("developmentOnly");
+		assertThat(build.configurations().customizations()).singleElement().satisfies((configuration) -> {
+			assertThat(configuration.getName()).isEqualTo("runtimeClasspath");
+			assertThat(configuration.getExtendsFrom()).containsOnly("developmentOnly");
+		});
+		Dependency devtools = build.dependencies().get("devtools");
+		assertThat(devtools).isInstanceOf(GradleDependency.class);
+		assertThat(((GradleDependency) devtools).getConfiguration()).isEqualTo("developmentOnly");
+	}
+
+	@Test
+	void gradleWithDevtoolsAndSpringBoot23RC1OrLaterDoesNotCreateDevelopmentOnlyConfiguration() {
+		GradleBuild build = new GradleBuild();
+		build.dependencies().add("devtools", DEVTOOLS_DEPENDENCY);
+		build.dependencies().add("devtools", DEVTOOLS_DEPENDENCY);
+		new DevToolsGradleBuildCustomizer(Version.parse("2.3.0.RC1"), "devtools").customize(build);
+		assertThat(build.configurations().names()).isEmpty();
+		Dependency devtools = build.dependencies().get("devtools");
+		assertThat(devtools).isInstanceOf(GradleDependency.class);
+		assertThat(((GradleDependency) devtools).getConfiguration()).isEqualTo("developmentOnly");
+	}
+
+	@Test
+	void gradleWithoutDevtoolsAndSpringBootPriorTo23RC1DoesNotCreateDevelopmentOnlyConfiguration() {
+		GradleBuild build = new GradleBuild();
+		build.dependencies().add("web", mock(Dependency.class));
+		new DevToolsGradleBuildCustomizer(Version.parse("2.3.0.M4"), "devtools").customize(build);
+		assertThat(build.configurations().names()).isEmpty();
+		assertThat(build.dependencies().ids()).containsOnly("web");
+	}
+
+}
diff --git a/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsMavenBuildCustomizerTests.java b/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsMavenBuildCustomizerTests.java
new file mode 100644
index 00000000..df46b36c
--- /dev/null
+++ b/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/dependency/devtools/DevToolsMavenBuildCustomizerTests.java
@@ -0,0 +1,56 @@
+/*
+ * Copyright 2012-2020 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package io.spring.initializr.generator.spring.dependency.devtools;
+
+import io.spring.initializr.generator.buildsystem.Dependency;
+import io.spring.initializr.generator.buildsystem.maven.MavenBuild;
+import io.spring.initializr.generator.buildsystem.maven.MavenDependency;
+import org.junit.jupiter.api.Test;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.mockito.Mockito.mock;
+
+/**
+ * Tests for {@link DevToolsMavenBuildCustomizer}.
+ *
+ * @author Stephane Nicoll
+ */
+class DevToolsMavenBuildCustomizerTests {
+
+	private static final Dependency DEVTOOLS_DEPENDENCY = Dependency
+			.withCoordinates("org.springframework.boot", "spring-boot-devtools").build();
+
+	@Test
+	void mavenWithDevtoolsSwitchOptionalFlag() {
+		MavenBuild build = new MavenBuild();
+		build.dependencies().add("devtools", DEVTOOLS_DEPENDENCY);
+		new DevToolsMavenBuildCustomizer("devtools").customize(build);
+		Dependency devtools = build.dependencies().get("devtools");
+		assertThat(devtools).isInstanceOf(MavenDependency.class);
+		assertThat(((MavenDependency) devtools).isOptional()).isTrue();
+
+	}
+
+	@Test
+	void mavenWithoutDevtoolsDoesNotChangeDependencies() {
+		MavenBuild build = new MavenBuild();
+		build.dependencies().add("web", mock(Dependency.class));
+		new DevToolsMavenBuildCustomizer("devtools").customize(build);
+		assertThat(build.dependencies().ids()).containsOnly("web");
+	}
+
+}