diff --git a/spring-web/src/main/java/org/springframework/http/client/JdkClientHttpRequest.java b/spring-web/src/main/java/org/springframework/http/client/JdkClientHttpRequest.java
index 886b921aaf..3237f32adc 100644
--- a/spring-web/src/main/java/org/springframework/http/client/JdkClientHttpRequest.java
+++ b/spring-web/src/main/java/org/springframework/http/client/JdkClientHttpRequest.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2002-2023 the original author or authors.
+ * Copyright 2002-2024 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -28,8 +28,11 @@ import java.time.Duration;
 import java.util.Collections;
 import java.util.Set;
 import java.util.TreeSet;
+import java.util.concurrent.ExecutionException;
 import java.util.concurrent.Executor;
 import java.util.concurrent.Flow;
+import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
 
 import org.springframework.http.HttpHeaders;
 import org.springframework.http.HttpMethod;
@@ -90,8 +93,14 @@ class JdkClientHttpRequest extends AbstractStreamingClientHttpRequest {
 	protected ClientHttpResponse executeInternal(HttpHeaders headers, @Nullable Body body) throws IOException {
 		try {
 			HttpRequest request = buildRequest(headers, body);
-			HttpResponse<InputStream> response =
-					this.httpClient.send(request, HttpResponse.BodyHandlers.ofInputStream());
+			HttpResponse<InputStream> response;
+			if (this.timeout != null) {
+				response = this.httpClient.sendAsync(request, HttpResponse.BodyHandlers.ofInputStream())
+						.get(this.timeout.toMillis(), TimeUnit.MILLISECONDS);
+			}
+			else {
+				response = this.httpClient.send(request, HttpResponse.BodyHandlers.ofInputStream());
+			}
 			return new JdkClientHttpResponse(response);
 		}
 		catch (UncheckedIOException ex) {
@@ -99,7 +108,26 @@ class JdkClientHttpRequest extends AbstractStreamingClientHttpRequest {
 		}
 		catch (InterruptedException ex) {
 			Thread.currentThread().interrupt();
-			throw new IOException("Could not send request: " + ex.getMessage(), ex);
+			throw new IOException("Request was interrupted: " + ex.getMessage(), ex);
+		}
+		catch (ExecutionException ex) {
+			Throwable cause = ex.getCause();
+
+			if (cause instanceof UncheckedIOException uioEx) {
+				throw uioEx.getCause();
+			}
+			if (cause instanceof RuntimeException rtEx) {
+				throw rtEx;
+			}
+			else if (cause instanceof IOException ioEx) {
+				throw ioEx;
+			}
+			else {
+				throw new IOException(cause.getMessage(), cause);
+			}
+		}
+		catch (TimeoutException ex) {
+			throw new IOException("Request timed out: " + ex.getMessage(), ex);
 		}
 	}