diff --git a/jetty-core/jetty-server/src/main/java/org/eclipse/jetty/server/handler/ContextRequest.java b/jetty-core/jetty-server/src/main/java/org/eclipse/jetty/server/handler/ContextRequest.java
index 8498ed36afee..1a4eb4b30196 100644
--- a/jetty-core/jetty-server/src/main/java/org/eclipse/jetty/server/handler/ContextRequest.java
+++ b/jetty-core/jetty-server/src/main/java/org/eclipse/jetty/server/handler/ContextRequest.java
@@ -13,7 +13,9 @@
 
 package org.eclipse.jetty.server.handler;
 
+import java.util.concurrent.TimeoutException;
 import java.util.function.Consumer;
+import java.util.function.Predicate;
 
 import org.eclipse.jetty.server.Context;
 import org.eclipse.jetty.server.Request;
@@ -39,6 +41,12 @@ public void demand(Runnable demandCallback)
         super.demand(new OnContextDemand(demandCallback));
     }
 
+    @Override
+    public void addIdleTimeoutListener(Predicate<TimeoutException> onIdleTimeout)
+    {
+        super.addIdleTimeoutListener(t -> _context.test(onIdleTimeout, t, ContextRequest.this));
+    }
+
     @Override
     public void addFailureListener(Consumer<Throwable> onFailure)
     {
diff --git a/jetty-core/jetty-server/src/test/java/org/eclipse/jetty/server/ServerTest.java b/jetty-core/jetty-server/src/test/java/org/eclipse/jetty/server/ServerTest.java
index ca79b2e15267..b2cf089d6d23 100644
--- a/jetty-core/jetty-server/src/test/java/org/eclipse/jetty/server/ServerTest.java
+++ b/jetty-core/jetty-server/src/test/java/org/eclipse/jetty/server/ServerTest.java
@@ -17,6 +17,7 @@
 import java.util.ArrayList;
 import java.util.List;
 import java.util.concurrent.CompletableFuture;
+import java.util.concurrent.CountDownLatch;
 import java.util.concurrent.TimeUnit;
 import java.util.concurrent.TimeoutException;
 import java.util.concurrent.atomic.AtomicReference;
@@ -30,6 +31,7 @@
 import org.eclipse.jetty.io.Content;
 import org.eclipse.jetty.io.EndPoint;
 import org.eclipse.jetty.io.QuietException;
+import org.eclipse.jetty.server.handler.ContextHandler;
 import org.eclipse.jetty.server.internal.HttpChannelState;
 import org.eclipse.jetty.server.internal.HttpConnection;
 import org.eclipse.jetty.util.Blocker;
@@ -48,11 +50,14 @@
 import static org.hamcrest.Matchers.instanceOf;
 import static org.hamcrest.Matchers.is;
 import static org.hamcrest.Matchers.not;
+import static org.hamcrest.Matchers.sameInstance;
+import static org.junit.jupiter.api.Assertions.assertTrue;
 
 public class ServerTest
 {
     private static final long IDLE_TIMEOUT = 1000L;
     private Server _server;
+    private ContextHandler _context;
     private LocalConnector _connector;
     private final AtomicReference<Runnable> _afterHandle = new AtomicReference<>();
 
@@ -60,6 +65,8 @@ public class ServerTest
     public void prepare() throws Exception
     {
         _server = new Server();
+        _context = new ContextHandler("/");
+        _server.setHandler(_context);
         _connector = new LocalConnector(_server, new HttpConnectionFactory()
         {
             @Override
@@ -116,7 +123,7 @@ public void dispose() throws Exception
     @Test
     public void testSimpleGET() throws Exception
     {
-        _server.setHandler(new Handler.Abstract()
+        _context.setHandler(new Handler.Abstract()
         {
             @Override
             public boolean handle(Request request, Response response, Callback callback)
@@ -161,7 +168,7 @@ public static Stream<Arguments> completionScenarios()
     @MethodSource("completionScenarios")
     public void testCompletion(boolean succeeded, boolean handling, boolean written, boolean last) throws Exception
     {
-        _server.setHandler(new Handler.Abstract(Invocable.InvocationType.BLOCKING)
+        _context.setHandler(new Handler.Abstract(Invocable.InvocationType.BLOCKING)
         {
             @Override
             public boolean handle(Request request, Response response, Callback callback) throws Exception
@@ -222,7 +229,7 @@ public boolean handle(Request request, Response response, Callback callback) thr
     public void testIdleTimeoutNoListener() throws Exception
     {
         // See ServerTimeoutsTest for more complete idle timeout testing.
-        _server.setHandler(new Handler.Abstract()
+        _context.setHandler(new Handler.Abstract()
         {
             @Override
             public boolean handle(Request request, Response response, Callback callback)
@@ -249,7 +256,7 @@ public void testIdleTimeoutNoListenerHttpConfigurationOnly() throws Exception
     {
         // See ServerTimeoutsTest for more complete idle timeout testing.
 
-        _server.setHandler(new Handler.Abstract()
+        _context.setHandler(new Handler.Abstract()
         {
             @Override
             public boolean handle(Request request, Response response, Callback callback)
@@ -280,7 +287,7 @@ public void testIdleTimeoutFalseListener() throws Exception
     {
         // See ServerTimeoutsTest for more complete idle timeout testing.
         CompletableFuture<Callback> callbackOnTimeout = new CompletableFuture<>();
-        _server.setHandler(new Handler.Abstract()
+        _context.setHandler(new Handler.Abstract()
         {
             @Override
             public boolean handle(Request request, Response response, Callback callback)
@@ -311,7 +318,7 @@ public void testIdleTimeoutWriteCallback() throws Exception
     {
         CompletableFuture<Throwable> onTimeout = new CompletableFuture<>();
         CompletableFuture<Throwable> writeFail = new CompletableFuture<>();
-        _server.setHandler(new Handler.Abstract()
+        _context.setHandler(new Handler.Abstract()
         {
             @Override
             public boolean handle(Request request, Response response, Callback callback)
@@ -355,4 +362,49 @@ public void run()
             assertThat(x, instanceOf(TimeoutException.class));
         }
     }
+
+    @Test
+    public void testListenersInContext() throws Exception
+    {
+        CountDownLatch latch = new CountDownLatch(3);
+        _context.setHandler(new Handler.Abstract()
+        {
+            @Override
+            public boolean handle(Request request, Response response, Callback callback)
+            {
+                assertThat(ContextHandler.getCurrentContext(), sameInstance(_context.getContext()));
+                latch.countDown();
+
+                request.addIdleTimeoutListener(t ->
+                {
+                    assertThat(ContextHandler.getCurrentContext(), sameInstance(_context.getContext()));
+                    latch.countDown();
+                    return true;
+                });
+
+                request.addFailureListener(t ->
+                {
+                    assertThat(ContextHandler.getCurrentContext(), sameInstance(_context.getContext()));
+                    latch.countDown();
+                });
+                return true;
+            }
+        });
+        _server.start();
+
+        String request = """
+                GET /path HTTP/1.0\r
+                Host: hostname\r
+                \r
+                """;
+
+        try (LocalConnector.LocalEndPoint localEndPoint = _connector.executeRequest(request))
+        {
+            assertTrue(latch.await(3 * IDLE_TIMEOUT, TimeUnit.MILLISECONDS));
+            String rawResponse = localEndPoint.getResponse();
+            HttpTester.Response response = HttpTester.parseResponse(rawResponse);
+            assertThat(response.getStatus(), is(HttpStatus.INTERNAL_SERVER_ERROR_500));
+        }
+    }
+
 }