diff --git a/spring-cloud-context/src/main/java/org/springframework/cloud/bootstrap/BootstrapApplicationListener.java b/spring-cloud-context/src/main/java/org/springframework/cloud/bootstrap/BootstrapApplicationListener.java
index 8346c63e..76428941 100644
--- a/spring-cloud-context/src/main/java/org/springframework/cloud/bootstrap/BootstrapApplicationListener.java
+++ b/spring-cloud-context/src/main/java/org/springframework/cloud/bootstrap/BootstrapApplicationListener.java
@@ -133,8 +133,8 @@ public class BootstrapApplicationListener
 			}
 			sources.add(cls);
 		}
-		builder.sources(sources.toArray(new Class[sources.size()]));
 		AnnotationAwareOrderComparator.sort(sources);
+		builder.sources(sources.toArray(new Class[sources.size()]));
 		final ConfigurableApplicationContext context = builder.run();
 		// Make the bootstrap context a parent of the app context
 		addAncestorInitializer(application, context);
diff --git a/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/BootstrapSourcesOrderingTests.java b/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/BootstrapSourcesOrderingTests.java
new file mode 100644
index 00000000..84df3ad0
--- /dev/null
+++ b/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/BootstrapSourcesOrderingTests.java
@@ -0,0 +1,34 @@
+package org.springframework.cloud.bootstrap;
+
+import org.junit.Test;
+import org.junit.runner.RunWith;
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.autoconfigure.EnableAutoConfiguration;
+import org.springframework.boot.test.context.SpringBootTest;
+import org.springframework.cloud.bootstrap.BootstrapOrderingSpringApplicationJsonIntegrationTests.Application;
+import org.springframework.context.annotation.Configuration;
+import org.springframework.core.env.ConfigurableEnvironment;
+import org.springframework.test.context.junit4.SpringRunner;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.springframework.cloud.bootstrap.TestHigherPriorityBootstrapConfiguration.firstToBeCreated;
+
+@RunWith(SpringRunner.class)
+@SpringBootTest(classes = Application.class)
+public class BootstrapSourcesOrderingTests {
+
+	@Autowired
+	private ConfigurableEnvironment environment;
+
+	@Test
+	public void sourcesAreOrderedCorrectly() {
+		Class<?> firstConstructedClass = firstToBeCreated.get();
+		assertThat(firstConstructedClass).as("bootstrap sources not ordered correctly").isEqualTo(TestHigherPriorityBootstrapConfiguration.class);
+	}
+
+	@EnableAutoConfiguration
+	@Configuration
+	protected static class Application {
+	}
+
+}
diff --git a/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/TestBootstrapConfiguration.java b/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/TestBootstrapConfiguration.java
new file mode 100644
index 00000000..798db7b8
--- /dev/null
+++ b/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/TestBootstrapConfiguration.java
@@ -0,0 +1,17 @@
+package org.springframework.cloud.bootstrap;
+
+import org.springframework.core.annotation.Order;
+
+import static org.springframework.cloud.bootstrap.TestHigherPriorityBootstrapConfiguration.firstToBeCreated;
+
+/**
+ * @author Spencer Gibb
+ */
+@Order(0)
+public class TestBootstrapConfiguration {
+
+	public TestBootstrapConfiguration() {
+		firstToBeCreated.compareAndSet(null, TestBootstrapConfiguration.class);
+	}
+
+}
diff --git a/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/TestHigherPriorityBootstrapConfiguration.java b/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/TestHigherPriorityBootstrapConfiguration.java
new file mode 100644
index 00000000..2494a5b6
--- /dev/null
+++ b/spring-cloud-context/src/test/java/org/springframework/cloud/bootstrap/TestHigherPriorityBootstrapConfiguration.java
@@ -0,0 +1,20 @@
+package org.springframework.cloud.bootstrap;
+
+import java.util.concurrent.atomic.AtomicReference;
+
+import org.springframework.core.Ordered;
+import org.springframework.core.annotation.Order;
+
+/**
+ * @author Spencer Gibb
+ */
+@Order(Ordered.HIGHEST_PRECEDENCE)
+public class TestHigherPriorityBootstrapConfiguration {
+
+	static final AtomicReference<Class<?>> firstToBeCreated = new AtomicReference<>();
+
+	public TestHigherPriorityBootstrapConfiguration() {
+		firstToBeCreated.compareAndSet(null, TestHigherPriorityBootstrapConfiguration.class);
+	}
+
+}
diff --git a/spring-cloud-context/src/test/resources/META-INF/spring.factories b/spring-cloud-context/src/test/resources/META-INF/spring.factories
new file mode 100644
index 00000000..419787be
--- /dev/null
+++ b/spring-cloud-context/src/test/resources/META-INF/spring.factories
@@ -0,0 +1,4 @@
+# Bootstrap components
+org.springframework.cloud.bootstrap.BootstrapConfiguration=\
+org.springframework.cloud.bootstrap.TestBootstrapConfiguration,\
+org.springframework.cloud.bootstrap.TestHigherPriorityBootstrapConfiguration