diff --git a/spring-kafka/src/main/java/org/springframework/kafka/listener/adapter/MessagingMessageListenerAdapter.java b/spring-kafka/src/main/java/org/springframework/kafka/listener/adapter/MessagingMessageListenerAdapter.java
index f1cc77b3c6..7275a1b446 100644
--- a/spring-kafka/src/main/java/org/springframework/kafka/listener/adapter/MessagingMessageListenerAdapter.java
+++ b/spring-kafka/src/main/java/org/springframework/kafka/listener/adapter/MessagingMessageListenerAdapter.java
@@ -80,6 +80,7 @@
  * @author Gary Russell
  * @author Artem Bilan
  * @author Venil Noronha
+ * @author Nathan Xu
  */
 public abstract class MessagingMessageListenerAdapter<K, V> implements ConsumerSeekAware {
 
@@ -470,8 +471,8 @@ protected void sendResponse(Object result, String topic, @Nullable Object source
 		if (!returnTypeMessage && topic == null) {
 			this.logger.debug(() -> "No replyTopic to handle the reply: " + result);
 		}
-		else if (result instanceof Message) {
-			Message<?> reply = checkHeaders(result, topic, source);
+		else if (result instanceof Message<?> mResult) {
+			Message<?> reply = checkHeaders(mResult, topic, source);
 			this.replyTemplate.send(reply);
 		}
 		else {
@@ -483,8 +484,9 @@ else if (result instanceof Message) {
 				}
 				if (iterableOfMessages || this.splitIterables) {
 					((Iterable<V>) result).forEach(v -> {
-						if (v instanceof Message) {
-							this.replyTemplate.send((Message<?>) v);
+						if (v instanceof Message<?> mv) {
+							Message<?> aReply = checkHeaders(mv, topic, source);
+							this.replyTemplate.send(aReply);
 						}
 						else {
 							this.replyTemplate.send(topic, v);
@@ -501,12 +503,12 @@ else if (result instanceof Message) {
 		}
 	}
 
-	private Message<?> checkHeaders(Object result, String topic, @Nullable Object source) { // NOSONAR (complexity)
-		Message<?> reply = (Message<?>) result;
+	private Message<?> checkHeaders(Message<?> reply, @Nullable String topic, @Nullable Object source) { // NOSONAR (complexity)
 		MessageHeaders headers = reply.getHeaders();
-		boolean needsTopic = headers.get(KafkaHeaders.TOPIC) == null;
+		boolean needsTopic = topic != null && headers.get(KafkaHeaders.TOPIC) == null;
 		boolean sourceIsMessage = source instanceof Message;
-		boolean needsCorrelation = headers.get(this.correlationHeaderName) == null && sourceIsMessage;
+		boolean needsCorrelation = headers.get(this.correlationHeaderName) == null && sourceIsMessage
+				&& getCorrelation((Message<?>) source) != null;
 		boolean needsPartition = headers.get(KafkaHeaders.PARTITION) == null && sourceIsMessage
 				&& getReplyPartition((Message<?>) source) != null;
 		if (needsTopic || needsCorrelation || needsPartition) {
@@ -514,11 +516,10 @@ private Message<?> checkHeaders(Object result, String topic, @Nullable Object so
 			if (needsTopic) {
 				builder.setHeader(KafkaHeaders.TOPIC, topic);
 			}
-			if (needsCorrelation && sourceIsMessage) {
-				builder.setHeader(this.correlationHeaderName,
-						((Message<?>) source).getHeaders().get(this.correlationHeaderName));
+			if (needsCorrelation) {
+				setCorrelation(builder, (Message<?>) source);
 			}
-			if (sourceIsMessage && reply.getHeaders().get(KafkaHeaders.REPLY_PARTITION) == null) {
+			if (needsPartition) {
 				setPartition(builder, (Message<?>) source);
 			}
 			reply = builder.build();
@@ -531,8 +532,8 @@ private void sendSingleResult(Object result, String topic, @Nullable Object sour
 		byte[] correlationId = null;
 		boolean sourceIsMessage = source instanceof Message;
 		if (sourceIsMessage
-				&& ((Message<?>) source).getHeaders().get(this.correlationHeaderName) != null) {
-			correlationId = ((Message<?>) source).getHeaders().get(this.correlationHeaderName, byte[].class);
+				&& getCorrelation((Message<?>) source) != null) {
+			correlationId = getCorrelation((Message<?>) source);
 		}
 		if (sourceIsMessage) {
 			sendReplyForMessageSource(result, topic, source, correlationId);
@@ -571,6 +572,18 @@ private void sendReplyForMessageSource(Object result, String topic, Object sourc
 		this.replyTemplate.send(builder.build());
 	}
 
+	private void setCorrelation(MessageBuilder<?> builder, Message<?> source) {
+		byte[] correlationBytes = getCorrelation(source);
+		if (correlationBytes != null) {
+			builder.setHeader(this.correlationHeaderName, correlationBytes);
+		}
+	}
+
+	@Nullable
+	private byte[] getCorrelation(Message<?> source) {
+		return source.getHeaders().get(this.correlationHeaderName, byte[].class);
+	}
+
 	private void setPartition(MessageBuilder<?> builder, Message<?> source) {
 		byte[] partitionBytes = getReplyPartition(source);
 		if (partitionBytes != null) {
diff --git a/spring-kafka/src/test/java/org/springframework/kafka/requestreply/ReplyingKafkaTemplateTests.java b/spring-kafka/src/test/java/org/springframework/kafka/requestreply/ReplyingKafkaTemplateTests.java
index 319221d7c6..dd7e406701 100644
--- a/spring-kafka/src/test/java/org/springframework/kafka/requestreply/ReplyingKafkaTemplateTests.java
+++ b/spring-kafka/src/test/java/org/springframework/kafka/requestreply/ReplyingKafkaTemplateTests.java
@@ -100,6 +100,7 @@
 
 /**
  * @author Gary Russell
+ * @author Nathan Xu
  * @since 2.1.3
  *
  */
@@ -116,7 +117,8 @@
 		ReplyingKafkaTemplateTests.I_REPLY, ReplyingKafkaTemplateTests.I_REQUEST,
 		ReplyingKafkaTemplateTests.J_REPLY, ReplyingKafkaTemplateTests.J_REQUEST,
 		ReplyingKafkaTemplateTests.K_REPLY, ReplyingKafkaTemplateTests.K_REQUEST,
-		ReplyingKafkaTemplateTests.L_REPLY, ReplyingKafkaTemplateTests.L_REQUEST })
+		ReplyingKafkaTemplateTests.L_REPLY, ReplyingKafkaTemplateTests.L_REQUEST,
+		ReplyingKafkaTemplateTests.M_REPLY, ReplyingKafkaTemplateTests.M_REQUEST })
 public class ReplyingKafkaTemplateTests {
 
 	public static final String A_REPLY = "aReply";
@@ -167,6 +169,10 @@ public class ReplyingKafkaTemplateTests {
 
 	public static final String L_REQUEST = "lRequest";
 
+	public static final String M_REPLY = "mReply";
+
+	public static final String M_REQUEST = "mRequest";
+
 	@Autowired
 	private EmbeddedKafkaBroker embeddedKafka;
 
@@ -845,6 +851,24 @@ void requestTimeoutWithMessage() throws Exception {
 		}
 	}
 
+	@Test
+	void testMessageIterableReturn() throws Exception {
+		ReplyingKafkaTemplate<Integer, String, String> template = createTemplate(M_REPLY);
+		try {
+			template.setDefaultReplyTimeout(Duration.ofSeconds(30));
+			Headers headers = new RecordHeaders();
+			ProducerRecord<Integer, String> record = new ProducerRecord<>(M_REQUEST, null, null, null, "foo", headers);
+			RequestReplyFuture<Integer, String, String> future = template.sendAndReceive(record);
+			future.getSendFuture().get(10, TimeUnit.SECONDS); // send ok
+			ConsumerRecord<Integer, String> consumerRecord = future.get(30, TimeUnit.SECONDS);
+			assertThat(consumerRecord.value()).isEqualTo("FOO");
+		}
+		finally {
+			template.stop();
+			template.destroy();
+		}
+	}
+
 	@Configuration
 	@EnableKafka
 	public static class Config {
@@ -1011,6 +1035,15 @@ public Message<String> handleL(String in) throws InterruptedException {
 					.build();
 		}
 
+		@KafkaListener(id = M_REQUEST, topics = M_REQUEST)
+		@SendTo  // default REPLY_TOPIC header
+		public List<Message<String>> handleM(String in) throws InterruptedException {
+			Message<String> message = MessageBuilder.withPayload(in.toUpperCase())
+					.setHeader("serverSentAnError", "user error")
+					.build();
+			return Collections.singletonList(message);
+		}
+
 	}
 
 	@KafkaListener(topics = C_REQUEST, groupId = C_REQUEST)