diff --git a/spring-integration-file/src/main/java/org/springframework/integration/file/FileWritingMessageHandler.java b/spring-integration-file/src/main/java/org/springframework/integration/file/FileWritingMessageHandler.java
index f8e2a416a0..7ef15b4309 100644
--- a/spring-integration-file/src/main/java/org/springframework/integration/file/FileWritingMessageHandler.java
+++ b/spring-integration-file/src/main/java/org/springframework/integration/file/FileWritingMessageHandler.java
@@ -391,7 +391,7 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 	}
 
 	@Override
-	public void stop() {
+	public synchronized void stop() {
 		if (this.flushTask != null) {
 			this.flushTask.cancel(true);
 			this.flushTask = null;
@@ -945,7 +945,7 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 			this.lock = lock;
 		}
 
-		private void close() {
+		private boolean close() {
 			try {
 				this.lock.lockInterruptibly();
 				try {
@@ -959,9 +959,11 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 				catch (IOException e) {
 					// ignore
 				}
+				return true;
 			}
 			catch (InterruptedException e1) {
 				Thread.currentThread().interrupt();
+				return false;
 			}
 			finally {
 				this.lock.unlock();
@@ -982,10 +984,14 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 					FileState state = entry.getValue();
 					if (state.lastWrite < expired ||
 							(!FileWritingMessageHandler.this.flushWhenIdle && state.firstWrite < expired)) {
-						iterator.remove();
-						state.close();
-						if (FileWritingMessageHandler.this.logger.isDebugEnabled()) {
-							FileWritingMessageHandler.this.logger.debug("Flushed: " + entry.getKey());
+						if (state.close()) {
+							if (FileWritingMessageHandler.this.logger.isDebugEnabled()) {
+								FileWritingMessageHandler.this.logger.debug("Flushed: " + entry.getKey());
+							}
+							iterator.remove();
+						}
+						else {
+							break; // interrupted
 						}
 					}
 				}