Handle direct CanncelationException on timeout in JdkClientHttpRequest

spring-web/src/main/java/org/springframework/http/client/JdkClientHttpRequest.java

@@ -37,6 +37,7 @@
 import java.util.concurrent.Executor;
 import java.util.concurrent.Flow;
 import java.util.concurrent.TimeUnit;
+import java.util.concurrent.atomic.AtomicBoolean;
 
 import org.jspecify.annotations.Nullable;
 
@@ -96,12 +97,13 @@ public URI getURI() {
 	@Override
 	protected ClientHttpResponse executeInternal(HttpHeaders headers, @Nullable Body body) throws IOException {
 		CompletableFuture<HttpResponse<InputStream>> responseFuture = null;
+		TimeoutHandler timeoutHandler = null;
 		try {
 			HttpRequest request = buildRequest(headers, body);
 			responseFuture = this.httpClient.sendAsync(request, HttpResponse.BodyHandlers.ofInputStream());
 
 			if (this.timeout != null) {
-				TimeoutHandler timeoutHandler = new TimeoutHandler(responseFuture, this.timeout);
+				timeoutHandler = new TimeoutHandler(responseFuture, this.timeout);
 				HttpResponse<InputStream> response = responseFuture.get();
 				InputStream inputStream = timeoutHandler.wrapInputStream(response);
 				return new JdkClientHttpResponse(response, inputStream);
@@ -120,7 +122,10 @@ protected ClientHttpResponse executeInternal(HttpHeaders headers, @Nullable Body
 			Throwable cause = ex.getCause();
 
 			if (cause instanceof CancellationException) {
-				throw new HttpTimeoutException("Request timed out");
+				if (timeoutHandler != null && timeoutHandler.isTimeout()) {
+					throw new HttpTimeoutException("Request timed out");
+				}
+				throw new IOException("Request was cancelled");
 			}
 			if (cause instanceof UncheckedIOException uioEx) {
 				throw uioEx.getCause();
@@ -136,6 +141,12 @@ else if (cause instanceof IOException ioEx) {
 				throw (message == null ? new IOException(cause) : new IOException(message, cause));
 			}
 		}
+		catch (CancellationException ex) {
+			if (timeoutHandler != null && timeoutHandler.isTimeout()) {
+				throw new HttpTimeoutException("Request timed out");
+			}
+			throw new IOException("Request was cancelled");
+		}
 	}
 
 	private HttpRequest buildRequest(HttpHeaders headers, @Nullable Body body) {
@@ -224,6 +235,7 @@ public ByteBuffer map(byte[] b, int off, int len) {
 	private static final class TimeoutHandler {
 
 		private final CompletableFuture<Void> timeoutFuture;
+		private final AtomicBoolean isTimeout = new AtomicBoolean(false);
 
 		private TimeoutHandler(CompletableFuture<HttpResponse<InputStream>> future, Duration timeout) {
 
@@ -232,6 +244,7 @@ private TimeoutHandler(CompletableFuture<HttpResponse<InputStream>> future, Dura
 
 			this.timeoutFuture.thenRun(() -> {
 				if (future.cancel(true) || future.isCompletedExceptionally() || !future.isDone()) {
+					isTimeout.set(true);
 					return;
 				}
 				try {
@@ -258,6 +271,10 @@ public void close() throws IOException {
 				}
 			};
 		}
+
+		public boolean isTimeout() {
+			return isTimeout.get();
+		}
 	}
 
 }

spring-web/src/test/java/org/springframework/http/client/JdkClientHttpRequestTest.java

@@ -0,0 +1,117 @@
+package org.springframework.http.client;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.junit.jupiter.api.Assertions.*;
+import static org.mockito.Mockito.*;
+
+import java.io.IOException;
+import java.io.InputStream;
+import java.net.URI;
+import java.net.http.HttpClient;
+import java.net.http.HttpRequest;
+import java.net.http.HttpResponse;
+import java.net.http.HttpTimeoutException;
+import java.time.Duration;
+import java.util.concurrent.*;
+
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.springframework.http.HttpHeaders;
+import org.springframework.http.HttpMethod;
+
+class JdkClientHttpRequestTest {
+
+	private HttpClient mockHttpClient;
+	private URI uri = URI.create("http://example.com");
+	private HttpMethod method = HttpMethod.GET;
+
+	private ExecutorService executor;
+
+	@BeforeEach
+	void setup() {
+		mockHttpClient = mock(HttpClient.class);
+		executor = Executors.newSingleThreadExecutor();
+	}
+
+	@AfterEach
+	void tearDown() {
+		executor.shutdownNow();
+	}
+
+	@Test
+	void executeInternal_withTimeout_shouldThrowHttpTimeoutException() throws Exception {
+		Duration timeout = Duration.ofMillis(10);
+
+		JdkClientHttpRequest request = new JdkClientHttpRequest(mockHttpClient, uri, method, executor, timeout);
+
+		CompletableFuture<HttpResponse<InputStream>> future = new CompletableFuture<>();
+
+		when(mockHttpClient.sendAsync(any(HttpRequest.class), any(HttpResponse.BodyHandler.class)))
+				.thenReturn(future);
+
+		HttpHeaders headers = new HttpHeaders();
+
+		CountDownLatch startLatch = new CountDownLatch(1);
+
+		// Cancellation thread waits for startLatch, then cancels the future after a delay
+		Thread canceller = new Thread(() -> {
+			try {
+				startLatch.await();
+				Thread.sleep(500);
+				future.cancel(true);
+			} catch (InterruptedException ignored) {
+			}
+		});
+		canceller.start();
+
+		IOException ex = assertThrows(IOException.class, () -> {
+			startLatch.countDown();
+			request.executeInternal(headers, null);
+		});
+
+		assertThat(ex)
+				.isInstanceOf(HttpTimeoutException.class)
+				.hasMessage("Request timed out");
+
+		canceller.join();
+	}
+
+	@Test
+	void executeInternal_withTimeout_shouldThrowIOException() throws Exception {
+		Duration timeout = Duration.ofMillis(500);
+
+		JdkClientHttpRequest request = new JdkClientHttpRequest(mockHttpClient, uri, method, executor, timeout);
+
+		CompletableFuture<HttpResponse<InputStream>> future = new CompletableFuture<>();
+
+		when(mockHttpClient.sendAsync(any(HttpRequest.class), any(HttpResponse.BodyHandler.class)))
+				.thenReturn(future);
+
+		HttpHeaders headers = new HttpHeaders();
+
+		CountDownLatch startLatch = new CountDownLatch(1);
+
+		Thread canceller = new Thread(() -> {
+			try {
+				startLatch.await();
+				Thread.sleep(10);
+				future.cancel(true);
+			} catch (InterruptedException ignored) {
+			}
+		});
+		canceller.start();
+
+		IOException ex = assertThrows(IOException.class, () -> {
+			startLatch.countDown();
+			request.executeInternal(headers, null);
+		});
+
+		assertThat(ex)
+				.isInstanceOf(IOException.class)
+				.hasMessage("Request was cancelled");
+
+		canceller.join();
+	}
+
+}