diff --git a/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java b/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java
index 2aec2da88d..d0110ffca3 100644
--- a/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java
+++ b/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java
@@ -77,38 +77,38 @@ import org.springframework.web.context.support.StandardServletEnvironment;
  * Classes that can be used to bootstrap and launch a Spring application from a Java main
  * method. By default class will perform the following steps to bootstrap your
  * application:
- * 
+ *
  * <ul>
  * <li>Create an appropriate {@link ApplicationContext} instance (depending on your
  * classpath)</li>
- * 
+ *
  * <li>Register a {@link CommandLinePropertySource} to expose command line arguments as
  * Spring properties</li>
- * 
+ *
  * <li>Refresh the application context, loading all singleton beans</li>
- * 
+ *
  * <li>Trigger any {@link CommandLineRunner} beans</li>
  * </ul>
- * 
+ *
  * In most circumstances the static {@link #run(Object, String[])} method can be called
  * directly from your {@literal main} method to bootstrap your application:
- * 
+ *
  * <pre class="code">
  * &#064;Configuration
  * &#064;EnableAutoConfiguration
  * public class MyApplication  {
- * 
+ *
  * // ... Bean definitions
- * 
+ *
  * public static void main(String[] args) throws Exception {
  *   SpringApplication.run(MyApplication.class, args);
  * }
  * </pre>
- * 
+ *
  * <p>
  * For more advanced configuration a {@link SpringApplication} instance can be created and
  * customized before being run:
- * 
+ *
  * <pre class="code">
  * public static void main(String[] args) throws Exception {
  *   SpringApplication app = new SpringApplication(MyApplication.class);
@@ -116,28 +116,29 @@ import org.springframework.web.context.support.StandardServletEnvironment;
  *   app.run(args)
  * }
  * </pre>
- * 
+ *
  * {@link SpringApplication}s can read beans from a variety of different sources. It is
  * generally recommended that a single {@code @Configuration} class is used to bootstrap
  * your application, however, any of the following sources can also be used:
- * 
+ *
  * <p>
  * <ul>
  * <li>{@link Class} - A Java class to be loaded by {@link AnnotatedBeanDefinitionReader}</li>
- * 
+ *
  * <li>{@link Resource} - An XML resource to be loaded by {@link XmlBeanDefinitionReader},
  * or a groovy script to be loaded by {@link GroovyBeanDefinitionReader}</li>
- * 
+ *
  * <li>{@link Package} - A Java package to be scanned by
  * {@link ClassPathBeanDefinitionScanner}</li>
- * 
+ *
  * <li>{@link CharSequence} - A class name, resource handle or package name to loaded as
  * appropriate. If the {@link CharSequence} cannot be resolved to class and does not
  * resolve to a {@link Resource} that exists it will be considered a {@link Package}.</li>
  * </ul>
- * 
+ *
  * @author Phillip Webb
  * @author Dave Syer
+ * @author Andy Wilkinson
  * @see #run(Object, String[])
  * @see #run(Object[], String[])
  * @see #SpringApplication(Object...)
@@ -151,7 +152,9 @@ public class SpringApplication {
 			+ "boot.context.embedded.AnnotationConfigEmbeddedWebApplicationContext";
 
 	private static final String[] WEB_ENVIRONMENT_CLASSES = { "javax.servlet.Servlet",
-			"org.springframework.web.context.ConfigurableWebApplicationContext" };
+	"org.springframework.web.context.ConfigurableWebApplicationContext" };
+
+	private static final String SYSTEM_PROPERTY_JAVA_AWT_HEADLESS = "java.awt.headless";
 
 	private final Log log = LogFactory.getLog(getClass());
 
@@ -262,7 +265,10 @@ public class SpringApplication {
 		stopWatch.start();
 		ConfigurableApplicationContext context = null;
 
-		System.setProperty("java.awt.headless", Boolean.toString(this.headless));
+		System.setProperty(
+				SYSTEM_PROPERTY_JAVA_AWT_HEADLESS,
+				System.getProperty(SYSTEM_PROPERTY_JAVA_AWT_HEADLESS,
+						Boolean.toString(this.headless)));
 
 		Collection<SpringApplicationRunListener> runListeners = getRunListeners(args);
 		for (SpringApplicationRunListener runListener : runListeners) {
@@ -540,7 +546,7 @@ public class SpringApplication {
 		if (this.resourceLoader != null) {
 			if (context instanceof GenericApplicationContext) {
 				((GenericApplicationContext) context)
-						.setResourceLoader(this.resourceLoader);
+				.setResourceLoader(this.resourceLoader);
 			}
 			if (context instanceof DefaultResourceLoader) {
 				((DefaultResourceLoader) context).setClassLoader(this.resourceLoader
@@ -573,7 +579,7 @@ public class SpringApplication {
 	protected void logStartupInfo(boolean isRoot) {
 		if (isRoot) {
 			new StartupInfoLogger(this.mainApplicationClass)
-					.logStarting(getApplicationLog());
+			.logStarting(getApplicationLog());
 		}
 	}
 
diff --git a/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java b/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
index 23ab071b89..445c448226 100644
--- a/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
+++ b/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
@@ -23,6 +23,7 @@ import java.util.Set;
 import java.util.concurrent.atomic.AtomicReference;
 
 import org.junit.After;
+import org.junit.Before;
 import org.junit.Rule;
 import org.junit.Test;
 import org.junit.rules.ExpectedException;
@@ -78,12 +79,15 @@ import static org.mockito.Mockito.verify;
 
 /**
  * Tests for {@link SpringApplication}.
- * 
+ *
  * @author Phillip Webb
  * @author Dave Syer
+ * @author Andy Wilkinson
  */
 public class SpringApplicationTests {
 
+	private String headlessProperty;
+
 	@Rule
 	public ExpectedException thrown = ExpectedException.none();
 
@@ -96,6 +100,23 @@ public class SpringApplicationTests {
 		throw new IllegalStateException("Could not obtain Environment");
 	}
 
+	@Before
+	public void storeAndClearHeadlessProperty() {
+		this.headlessProperty = System.getProperty("java.awt.headless");
+		System.clearProperty("java.awt.headless");
+	}
+
+	@After
+	public void reinstateHeadlessProperty() {
+		if (this.headlessProperty == null) {
+			System.clearProperty("java.awt.headless");
+		}
+		else {
+			System.setProperty("java.awt.headless", this.headlessProperty);
+		}
+
+	}
+
 	@After
 	public void close() {
 		if (this.context != null) {
@@ -504,6 +525,15 @@ public class SpringApplicationTests {
 		assertThat(System.getProperty("java.awt.headless"), equalTo("false"));
 	}
 
+	@Test
+	public void headlessSystemPropertyTakesPrecedence() throws Exception {
+		System.setProperty("java.awt.headless", "false");
+		TestSpringApplication application = new TestSpringApplication(ExampleConfig.class);
+		application.setWebEnvironment(false);
+		application.run();
+		assertThat(System.getProperty("java.awt.headless"), equalTo("false"));
+	}
+
 	private boolean hasPropertySource(ConfigurableEnvironment environment,
 			Class<?> propertySourceClass, String name) {
 		for (PropertySource<?> source : environment.getPropertySources()) {