diff --git a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/HttpMessageConverters.java b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/HttpMessageConverters.java
index ac52b71fd98..f779ffff6b7 100644
--- a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/HttpMessageConverters.java
+++ b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/HttpMessageConverters.java
@@ -67,16 +67,27 @@ public class HttpMessageConverters implements Iterable<HttpMessageConverter<?>>
 	/**
 	 * Create a new {@link HttpMessageConverters} instance with the specified additional
 	 * converters.
-	 * @param additionalConverters additional converters to be added. New converters will
-	 * be added to the front of the list, overrides will replace existing items without
-	 * changing the order. The {@link #getConverters()} methods can be used for further
-	 * converter manipulation.
+	 * @param additionalConverters additional converters to be added. Items are added just
+	 * before any default converter of the same type (or at the front of the list if no
+	 * default converter is found) The {@link #getConverters()} methods can be used for
+	 * further converter manipulation.
 	 */
 	public HttpMessageConverters(Collection<HttpMessageConverter<?>> additionalConverters) {
 		List<HttpMessageConverter<?>> converters = new ArrayList<HttpMessageConverter<?>>();
-		List<HttpMessageConverter<?>> defaultConverters = getDefaultConverters();
-		converters.addAll(additionalConverters);
-		converters.addAll(defaultConverters);
+		List<HttpMessageConverter<?>> processing = new ArrayList<HttpMessageConverter<?>>(
+				additionalConverters);
+		for (HttpMessageConverter<?> defaultConverter : getDefaultConverters()) {
+			Iterator<HttpMessageConverter<?>> iterator = processing.iterator();
+			while (iterator.hasNext()) {
+				HttpMessageConverter<?> candidate = iterator.next();
+				if (ClassUtils.isAssignableValue(defaultConverter.getClass(), candidate)) {
+					converters.add(candidate);
+					iterator.remove();
+				}
+			}
+			converters.add(defaultConverter);
+		}
+		converters.addAll(0, processing);
 		this.converters = Collections.unmodifiableList(converters);
 	}
 
diff --git a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/HttpMessageConvertersTests.java b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/HttpMessageConvertersTests.java
index 49ad34abf80..91ae26af35e 100644
--- a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/HttpMessageConvertersTests.java
+++ b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/HttpMessageConvertersTests.java
@@ -34,6 +34,7 @@ import org.springframework.http.converter.xml.SourceHttpMessageConverter;
 
 import static org.hamcrest.Matchers.equalTo;
 import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertNotEquals;
 import static org.junit.Assert.assertThat;
 import static org.junit.Assert.assertTrue;
 import static org.mockito.Mockito.mock;
@@ -65,27 +66,35 @@ public class HttpMessageConvertersTests {
 	}
 
 	@Test
-	public void overrideExistingConverter() {
-		MappingJackson2HttpMessageConverter converter = new MappingJackson2HttpMessageConverter();
-		HttpMessageConverters converters = new HttpMessageConverters(converter);
-		assertTrue(converters.getConverters().contains(converter));
-		int count = 0;
-		for (HttpMessageConverter<?> httpMessageConverter : converters) {
-			if (httpMessageConverter instanceof MappingJackson2HttpMessageConverter) {
-				count++;
+	public void addBeforeExistingConverter() {
+		MappingJackson2HttpMessageConverter converter1 = new MappingJackson2HttpMessageConverter();
+		MappingJackson2HttpMessageConverter converter2 = new MappingJackson2HttpMessageConverter();
+		HttpMessageConverters converters = new HttpMessageConverters(converter1,
+				converter2);
+		assertTrue(converters.getConverters().contains(converter1));
+		assertTrue(converters.getConverters().contains(converter2));
+		List<MappingJackson2HttpMessageConverter> httpConverters = new ArrayList<MappingJackson2HttpMessageConverter>();
+		for (HttpMessageConverter<?> candidate : converters) {
+			if (candidate instanceof MappingJackson2HttpMessageConverter) {
+				httpConverters.add((MappingJackson2HttpMessageConverter) candidate);
 			}
 		}
 		// The existing converter is still there, but with a lower priority
-		assertEquals(2, count);
-		assertEquals(0, converters.getConverters().indexOf(converter));
+		assertEquals(3, httpConverters.size());
+		assertEquals(0, httpConverters.indexOf(converter1));
+		assertEquals(1, httpConverters.indexOf(converter2));
+		assertNotEquals(0, converters.getConverters().indexOf(converter1));
 	}
 
 	@Test
-	public void addNewConverter() {
-		HttpMessageConverter<?> converter = mock(HttpMessageConverter.class);
-		HttpMessageConverters converters = new HttpMessageConverters(converter);
-		assertTrue(converters.getConverters().contains(converter));
-		assertEquals(converter, converters.getConverters().get(0));
+	public void addNewConverters() {
+		HttpMessageConverter<?> converter1 = mock(HttpMessageConverter.class);
+		HttpMessageConverter<?> converter2 = mock(HttpMessageConverter.class);
+		HttpMessageConverters converters = new HttpMessageConverters(converter1,
+				converter2);
+		assertTrue(converters.getConverters().contains(converter1));
+		assertEquals(converter1, converters.getConverters().get(0));
+		assertEquals(converter2, converters.getConverters().get(1));
 	}
 
 }