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 7ef15b4309..ef1813dceb 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
@@ -365,13 +365,13 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 		this.evaluationContext = ExpressionUtils.createStandardEvaluationContext(getBeanFactory());
 
 		if (this.destinationDirectoryExpression instanceof LiteralExpression) {
-			final File directory = new File(this.destinationDirectoryExpression.getValue(
-					this.evaluationContext, null, String.class));
+			String directoryPath = this.destinationDirectoryExpression.getValue(this.evaluationContext, String.class);
+			final File directory = new File(directoryPath);
 			validateDestinationDirectory(directory, this.autoCreateDirectory);
 		}
 
 		Assert.state(!(this.temporaryFileSuffixSet
-				&& (FileExistsMode.APPEND.equals(this.fileExistsMode)
+						&& (FileExistsMode.APPEND.equals(this.fileExistsMode)
 						|| FileExistsMode.APPEND_NO_FLUSH.equals(this.fileExistsMode))),
 				"'temporaryFileSuffix' can not be set when appending to an existing file");
 
@@ -391,12 +391,32 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 	}
 
 	@Override
-	public synchronized void stop() {
-		if (this.flushTask != null) {
-			this.flushTask.cancel(true);
-			this.flushTask = null;
+	public void stop() {
+		synchronized (this) {
+			if (this.flushTask != null) {
+				this.flushTask.cancel(true);
+				this.flushTask = null;
+			}
+		}
+		Flusher flusher = new Flusher();
+		flusher.run();
+		boolean needInterrupt = this.fileStates.size() > 0;
+		int n = 0;
+		while (n++ < 10 && this.fileStates.size() > 0) {
+			try {
+				Thread.sleep(1);
+			}
+			catch (InterruptedException e) {
+				// cancel the interrupt
+			}
+			flusher.run();
+		}
+		if (this.fileStates.size() > 0) {
+			this.logger.error("Failed to flush after multiple attempts, while stopping: " + this.fileStates.keySet());
+		}
+		if (needInterrupt) {
+			Thread.currentThread().interrupt();
 		}
-		new Flusher().run();
 	}
 
 	@Override
@@ -529,7 +549,7 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 	}
 
 	private File handleInputStreamMessage(final InputStream sourceFileInputStream, File originalFile, File tempFile,
-										  final File resultFile) throws IOException {
+			final File resultFile) throws IOException {
 		final boolean append = FileExistsMode.APPEND.equals(this.fileExistsMode)
 				|| FileExistsMode.APPEND_NO_FLUSH.equals(this.fileExistsMode);
 
@@ -796,10 +816,10 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 
 	private synchronized FileState getFileState(final File fileToWriteTo, boolean isString)
 			throws FileNotFoundException {
-		String absolutePath = fileToWriteTo.getAbsolutePath();
 		FileState state;
 		boolean appendNoFlush = FileExistsMode.APPEND_NO_FLUSH.equals(this.fileExistsMode);
 		if (appendNoFlush) {
+			String absolutePath = fileToWriteTo.getAbsolutePath();
 			state = this.fileStates.get(absolutePath);
 			if (state != null && ((isString && state.stream != null) || (!isString && state.writer != null))) {
 				state.close();
@@ -872,16 +892,19 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 	 * @param flushPredicate the {@link FlushPredicate}.
 	 * @since 4.3
 	 */
-	public synchronized void flushIfNeeded(FlushPredicate flushPredicate) {
-		Iterator<Entry<String, FileState>> iterator = FileWritingMessageHandler.this.fileStates.entrySet().iterator();
-		while (iterator.hasNext()) {
-			Entry<String, FileState> entry = iterator.next();
-			FileState state = entry.getValue();
-			if (flushPredicate.shouldFlush(entry.getKey(), state.lastWrite)) {
-				iterator.remove();
-				state.close();
-			}
-		}
+	public void flushIfNeeded(final FlushPredicate flushPredicate) {
+		flushIfNeeded(new MessageFlushPredicate() {
+
+						  @Override
+						  public boolean shouldFlush(String fileAbsolutePath, long lastWrite,
+								  Message<?> filterMessage) {
+
+							  return flushPredicate.shouldFlush(fileAbsolutePath, lastWrite);
+
+						  }
+
+					  },
+				null);
 	}
 
 	/**
@@ -893,16 +916,24 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 	 * @param filterMessage an optional message passed into the predicate.
 	 * @since 4.3
 	 */
-	public synchronized void flushIfNeeded(MessageFlushPredicate flushPredicate, Message<?> filterMessage) {
-		Iterator<Entry<String, FileState>> iterator = FileWritingMessageHandler.this.fileStates.entrySet().iterator();
-		while (iterator.hasNext()) {
-			Entry<String, FileState> entry = iterator.next();
-			FileState state = entry.getValue();
-			if (flushPredicate.shouldFlush(entry.getKey(), state.lastWrite, filterMessage)) {
-				iterator.remove();
-				state.close();
+	public void flushIfNeeded(MessageFlushPredicate flushPredicate, Message<?> filterMessage) {
+		doFlush(findFilesToFlush(flushPredicate, filterMessage));
+	}
+
+	private Map<String, FileState> findFilesToFlush(MessageFlushPredicate flushPredicate, Message<?> filterMessage) {
+		Map<String, FileState> toRemove = new HashMap<String, FileState>();
+		synchronized (this) {
+			Iterator<Entry<String, FileState>> iterator = this.fileStates.entrySet().iterator();
+			while (iterator.hasNext()) {
+				Entry<String, FileState> entry = iterator.next();
+				FileState state = entry.getValue();
+				if (flushPredicate.shouldFlush(entry.getKey(), state.lastWrite, filterMessage)) {
+					iterator.remove();
+					toRemove.put(entry.getKey(), state);
+				}
 			}
 		}
+		return toRemove;
 	}
 
 	private synchronized void clearState(final File fileToWriteTo, final FileState state) {
@@ -911,6 +942,33 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 		}
 	}
 
+	private void doFlush(Map<String, FileState> toRemove) {
+		Map<String, FileState> toRestore = new HashMap<String, FileState>();
+		boolean interrupted = false;
+		for (Entry<String, FileState> entry : toRemove.entrySet()) {
+			if (!interrupted && entry.getValue().close()) {
+				if (FileWritingMessageHandler.this.logger.isDebugEnabled()) {
+					FileWritingMessageHandler.this.logger.debug("Flushed: " + entry.getKey());
+				}
+			}
+			else { // interrupted (stop), re-add
+				interrupted = true;
+				toRestore.put(entry.getKey(), entry.getValue());
+			}
+		}
+		if (interrupted) {
+			if (FileWritingMessageHandler.this.logger.isDebugEnabled()) {
+				FileWritingMessageHandler.this.logger
+						.debug("Interrupted during flush; not flushed: " + toRestore.keySet());
+			}
+			synchronized (this) {
+				for (Entry<String, FileState> entry : toRestore.entrySet()) {
+					this.fileStates.putIfAbsent(entry.getKey(), entry.getValue());
+				}
+			}
+		}
+	}
+
 	private static boolean rename(File source, File target) throws IOException {
 		return (nioFilesPresent && filesMove(source, target)) || source.renameTo(target);
 	}
@@ -925,7 +983,7 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 
 		private final BufferedWriter writer;
 
-		private final BufferedOutputStream  stream;
+		private final BufferedOutputStream stream;
 
 		private final Lock lock;
 
@@ -975,6 +1033,7 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 
 		@Override
 		public void run() {
+			Map<String, FileState> toRemove = new HashMap<String, FileState>();
 			synchronized (FileWritingMessageHandler.this) {
 				long expired = FileWritingMessageHandler.this.flushTask == null ? Long.MAX_VALUE
 						: (System.currentTimeMillis() - FileWritingMessageHandler.this.flushInterval);
@@ -984,18 +1043,12 @@ public class FileWritingMessageHandler extends AbstractReplyProducingMessageHand
 					FileState state = entry.getValue();
 					if (state.lastWrite < expired ||
 							(!FileWritingMessageHandler.this.flushWhenIdle && state.firstWrite < expired)) {
-						if (state.close()) {
-							if (FileWritingMessageHandler.this.logger.isDebugEnabled()) {
-								FileWritingMessageHandler.this.logger.debug("Flushed: " + entry.getKey());
-							}
-							iterator.remove();
-						}
-						else {
-							break; // interrupted
-						}
+						toRemove.put(entry.getKey(), state);
+						iterator.remove();
 					}
 				}
 			}
+			doFlush(toRemove);
 		}
 
 	}