diff --git a/spring-integration-file/src/main/java/org/springframework/integration/file/outbound/FileWritingMessageHandler.java b/spring-integration-file/src/main/java/org/springframework/integration/file/outbound/FileWritingMessageHandler.java
index 9b8d2ca87b..e2f1d58e54 100644
--- a/spring-integration-file/src/main/java/org/springframework/integration/file/outbound/FileWritingMessageHandler.java
+++ b/spring-integration-file/src/main/java/org/springframework/integration/file/outbound/FileWritingMessageHandler.java
@@ -118,6 +118,7 @@
  * @author Christian Tzolov
  * @author Ngoc Nhan
  * @author Thomas Knall
+ * @author Jiwoo Lee
  *
  * @since 7.0
  */
@@ -674,24 +675,43 @@ private void appendStreamToFile(File fileToWriteTo, InputStream sourceFileInputS
 				bos.write(System.lineSeparator().getBytes());
 			}
 		}
-		finally {
-			cleanUpFileState(fileToWriteTo, state, bos);
+		catch (IOException | RuntimeException ex) {
+			cleanUpFileStateSuppressing(ex, fileToWriteTo, state, bos);
+			throw ex;
 		}
+		cleanUpFileState(fileToWriteTo, state, bos);
 	}
 
-	private void cleanUpFileState(File fileToWriteTo, @Nullable FileState state, @Nullable Closeable closeable) {
-		try {
-			if (state == null || this.flushTask == null) {
+	private void cleanUpFileState(File fileToWriteTo, @Nullable FileState state, @Nullable Closeable closeable)
+			throws IOException {
+
+		if (state == null || this.flushTask == null) {
+			try {
 				if (closeable != null) {
 					closeable.close();
 				}
-				clearState(fileToWriteTo, state);
 			}
-			else {
-				state.lastWrite = System.currentTimeMillis();
+			finally {
+				clearState(fileToWriteTo, state);
 			}
 		}
+		else {
+			state.lastWrite = System.currentTimeMillis();
+		}
+	}
+
+	/**
+	 * Clean up after a write that has already failed, adding any failure from the clean up
+	 * to the exception which is on its way out, the way try-with-resources does.
+	 */
+	private void cleanUpFileStateSuppressing(Throwable primary, File fileToWriteTo, @Nullable FileState state,
+			@Nullable Closeable closeable) {
+
+		try {
+			cleanUpFileState(fileToWriteTo, state, closeable);
+		}
 		catch (IOException ex) {
+			primary.addSuppressed(ex);
 		}
 	}
 
@@ -733,9 +753,11 @@ private void writeBytesToFile(File fileToWriteTo, boolean append, byte[] bytes)
 				bos.write(System.lineSeparator().getBytes());
 			}
 		}
-		finally {
-			cleanUpFileState(fileToWriteTo, state, bos);
+		catch (IOException | RuntimeException ex) {
+			cleanUpFileStateSuppressing(ex, fileToWriteTo, state, bos);
+			throw ex;
 		}
+		cleanUpFileState(fileToWriteTo, state, bos);
 	}
 
 	private File handleStringMessage(String content, @Nullable File originalFile, File tempFile, File resultFile,
@@ -776,9 +798,11 @@ private void writeStringToFile(File fileToWriteTo, boolean append, String conten
 				writer.newLine();
 			}
 		}
-		finally {
-			cleanUpFileState(fileToWriteTo, state, writer);
+		catch (IOException | RuntimeException ex) {
+			cleanUpFileStateSuppressing(ex, fileToWriteTo, state, writer);
+			throw ex;
 		}
+		cleanUpFileState(fileToWriteTo, state, writer);
 	}
 
 	private File determineFileToWrite(File resultFile, File tempFile) {
diff --git a/spring-integration-file/src/test/java/org/springframework/integration/file/outbound/FileWritingMessageHandlerTests.java b/spring-integration-file/src/test/java/org/springframework/integration/file/outbound/FileWritingMessageHandlerTests.java
index 05f33c3832..a7f9c89c46 100644
--- a/spring-integration-file/src/test/java/org/springframework/integration/file/outbound/FileWritingMessageHandlerTests.java
+++ b/spring-integration-file/src/test/java/org/springframework/integration/file/outbound/FileWritingMessageHandlerTests.java
@@ -17,12 +17,16 @@
 package org.springframework.integration.file.outbound;
 
 import java.io.BufferedOutputStream;
+import java.io.BufferedWriter;
 import java.io.ByteArrayInputStream;
 import java.io.File;
 import java.io.FileInputStream;
+import java.io.FileNotFoundException;
 import java.io.FileOutputStream;
+import java.io.FileWriter;
 import java.io.IOException;
 import java.io.InputStream;
+import java.io.Writer;
 import java.nio.file.Files;
 import java.nio.file.InvalidPathException;
 import java.nio.file.attribute.PosixFilePermission;
@@ -90,6 +94,7 @@
  * @author Alen Turkovic
  * @author Glenn Renfro
  * @author Thomas Knall
+ * @author Jiwoo Lee
  */
 public class FileWritingMessageHandlerTests implements TestApplicationContextAware {
 
@@ -776,4 +781,47 @@ protected File messageToFile(Message<?> result) {
 		return (File) result.getPayload();
 	}
 
+	@Test
+	void closeFailureIsReportedAndTheFileIsNotPromoted(@TempDir File localRoot) throws Exception {
+		File out = new File(localRoot, "out");
+		// A writer whose close() fails the way a full disk does: the buffered content
+		// never reaches the file and the IOException surfaces from close().
+		FileWritingMessageHandler handler = new FileWritingMessageHandler(out) {
+
+			@Override
+			protected BufferedWriter createWriter(File fileToWriteTo, boolean append)
+					throws FileNotFoundException {
+
+				Writer target;
+				try {
+					target = new FileWriter(fileToWriteTo, append);
+				}
+				catch (IOException ex) {
+					throw new FileNotFoundException(ex.getMessage());
+				}
+				return new BufferedWriter(target) {
+
+					@Override
+					public void close() throws IOException {
+						target.close();
+						throw new IOException("No space left on device");
+					}
+
+				};
+			}
+
+		};
+		handler.setFileNameGenerator(message -> "payload.txt");
+		handler.setOutputChannel(new NullChannel());
+		handler.setBeanFactory(TEST_INTEGRATION_CONTEXT);
+		handler.setApplicationContext(new GenericApplicationContext());
+		handler.afterPropertiesSet();
+
+		assertThatExceptionOfType(MessageHandlingException.class)
+				.isThrownBy(() -> handler.handleMessage(new GenericMessage<>("important payload")))
+				.withStackTraceContaining("java.io.IOException: No space left on device");
+
+		assertThat(new File(out, "payload.txt")).doesNotExist();
+	}
+
 }