diff --git a/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersion.java b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersion.java
index 3ee63942..e5f1c90b 100644
--- a/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersion.java
+++ b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersion.java
@@ -36,6 +36,11 @@ import org.springframework.context.annotation.Conditional;
 @Conditional(OnGradleVersionCondition.class)
 public @interface ConditionalOnGradleVersion {
 
-	String value();
+	/**
+	 * The Gradle generations that should be checked. The condition matches when at least
+	 * one gradle generation matches.
+	 * @return the gradle generation to check
+	 */
+	String[] value();
 
 }
diff --git a/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/OnGradleVersionCondition.java b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/OnGradleVersionCondition.java
index cb7df7bf..255ab9bb 100644
--- a/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/OnGradleVersionCondition.java
+++ b/initializr-generator-spring/src/main/java/io/spring/initializr/generator/spring/build/gradle/OnGradleVersionCondition.java
@@ -16,6 +16,8 @@
 
 package io.spring.initializr.generator.spring.build.gradle;
 
+import java.util.Arrays;
+
 import io.spring.initializr.generator.condition.ProjectGenerationCondition;
 import io.spring.initializr.generator.project.ResolvedProjectDescription;
 import io.spring.initializr.generator.version.Version;
@@ -43,15 +45,15 @@ public class OnGradleVersionCondition extends ProjectGenerationCondition {
 	@Override
 	protected boolean matches(ResolvedProjectDescription projectDescription,
 			ConditionContext context, AnnotatedTypeMetadata metadata) {
-		String gradleVersion = determineGradleGeneration(
+		String gradleGeneration = determineGradleGeneration(
 				projectDescription.getPlatformVersion());
-		if (gradleVersion == null) {
+		if (gradleGeneration == null) {
 			return false;
 		}
-		String value = (String) metadata
+		String[] values = (String[]) metadata
 				.getAnnotationAttributes(ConditionalOnGradleVersion.class.getName())
 				.get("value");
-		return gradleVersion.equals(value);
+		return Arrays.asList(values).contains(gradleGeneration);
 	}
 
 	private String determineGradleGeneration(Version platformVersion) {
diff --git a/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersionTests.java b/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersionTests.java
index 8c6b19b4..74f8ebc2 100644
--- a/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersionTests.java
+++ b/initializr-generator-spring/src/test/java/io/spring/initializr/generator/spring/build/gradle/ConditionalOnGradleVersionTests.java
@@ -16,6 +16,8 @@
 
 package io.spring.initializr.generator.spring.build.gradle;
 
+import java.util.Map;
+
 import io.spring.initializr.generator.project.ProjectDescription;
 import io.spring.initializr.generator.test.project.ProjectAssetTester;
 import io.spring.initializr.generator.version.Version;
@@ -71,6 +73,24 @@ public class ConditionalOnGradleVersionTests {
 		});
 	}
 
+	@Test
+	void outcomeWithSpringBoot15AndMultipleGenerations() {
+		ProjectDescription projectDescription = new ProjectDescription();
+		projectDescription.setPlatformVersion(Version.parse("1.5.18.RELEASE"));
+		Map<String, String> candidates = candidatesFor(projectDescription,
+				Gradle3Or4TestConfiguration.class);
+		assertThat(candidates).containsOnlyKeys("gradle3", "gradle3AndLater");
+	}
+
+	@Test
+	void outcomeWithSpringBoot2AndMultipleGenerations() {
+		ProjectDescription projectDescription = new ProjectDescription();
+		projectDescription.setPlatformVersion(Version.parse("2.0.9.RELEASE"));
+		Map<String, String> candidates = candidatesFor(projectDescription,
+				Gradle3Or4TestConfiguration.class);
+		assertThat(candidates).containsOnlyKeys("gradle4", "gradle3AndLater");
+	}
+
 	private String outcomeFor(ProjectDescription projectDescription) {
 		return this.projectTester.generate(projectDescription,
 				(projectGenerationContext) -> {
@@ -80,6 +100,12 @@ public class ConditionalOnGradleVersionTests {
 				});
 	}
 
+	private Map<String, String> candidatesFor(ProjectDescription projectDescription,
+			Class<?>... extraConfigurations) {
+		return this.projectTester.withConfiguration(extraConfigurations).generate(
+				projectDescription, (context) -> context.getBeansOfType(String.class));
+	}
+
 	@Configuration
 	static class GradleVersionTestConfiguration {
 
@@ -97,4 +123,15 @@ public class ConditionalOnGradleVersionTests {
 
 	}
 
+	@Configuration
+	static class Gradle3Or4TestConfiguration {
+
+		@Bean
+		@ConditionalOnGradleVersion({ "3", "4" })
+		public String gradle3AndLater() {
+			return "testGradle3AndLater";
+		}
+
+	}
+
 }