diff --git a/reactor-netty-core/src/main/java/reactor/netty/resources/DefaultLoopResources.java b/reactor-netty-core/src/main/java/reactor/netty/resources/DefaultLoopResources.java
index 8b3b4731d..87f3a0a55 100644
--- a/reactor-netty-core/src/main/java/reactor/netty/resources/DefaultLoopResources.java
+++ b/reactor-netty-core/src/main/java/reactor/netty/resources/DefaultLoopResources.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2011-2023 VMware, Inc. or its affiliates, All Rights Reserved.
+ * Copyright (c) 2011-2024 VMware, Inc. or its affiliates, All Rights Reserved.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -130,7 +130,8 @@ public Mono<Void> disposeLater(Duration quietPeriod, Duration timeout) {
 				}
 			}
 
-			return Mono.when(clMono, sslMono, slMono, cnclMono, cnslMono, cnsrvlMono);
+			return Mono.when(clMono, sslMono, slMono, cnclMono, cnslMono, cnsrvlMono)
+			           .timeout(timeout, Mono.error(new IllegalStateException("LoopResources couldn't be disposed within " + timeout.toMillis() + "ms")));
 		});
 	}
 
diff --git a/reactor-netty-http/src/test/java/reactor/netty/http/server/HttpServerTests.java b/reactor-netty-http/src/test/java/reactor/netty/http/server/HttpServerTests.java
index a8ac5bd09..86742bc8a 100644
--- a/reactor-netty-http/src/test/java/reactor/netty/http/server/HttpServerTests.java
+++ b/reactor-netty-http/src/test/java/reactor/netty/http/server/HttpServerTests.java
@@ -1910,6 +1910,73 @@ public void channelRead(@NotNull ChannelHandlerContext ctx, @NotNull Object msg)
 				.isEqualTo("delay500delay1000");
 	}
 
+	@Test
+	public void testGracefulShutdownIssue3509() throws Exception {
+		CountDownLatch connectionOpenedLatch = new CountDownLatch(2);
+		CountDownLatch connectionClosedLatch = new CountDownLatch(1);
+		CountDownLatch responseReceivedLatch = new CountDownLatch(1);
+		LoopResources loop = LoopResources.create("testGracefulShutdownIssue3509");
+		AtomicBoolean stop = new AtomicBoolean(false);
+		Sinks.One<String> delay = Sinks.one();
+		this.disposableServer =
+				createServer().runOn(loop)
+				              .doOnConnection(c -> {
+				                  c.onDispose().subscribe(null, null, connectionClosedLatch::countDown);
+				                  connectionOpenedLatch.countDown();
+				              })
+				              // Register a channel group, when invoking disposeNow()
+				              // the implementation will wait for the active requests to finish
+				              .channelGroup(new DefaultChannelGroup(new DefaultEventExecutor()))
+				              .route(r ->
+				                  r.get("/delay", (req, res) -> res.sendString(delay.asMono()))
+				                   .get("/cpuIntensive", (req, res) -> {
+				                       // Simulate some long-running CPU-intensive work
+				                       while (!stop.get()) {
+				                       // this is deliberate
+				                       }
+				                       return res.sendString(Mono.just("cpuIntensive"));
+				                   }))
+				              .bindNow(Duration.ofSeconds(30));
+
+		HttpClient client = createClient(this.disposableServer::address);
+
+		AtomicReference<String> result = new AtomicReference<>();
+		Flux.just("/delay", "/cpuIntensive")
+		    .flatMap(s -> client.get().uri(s).responseContent().aggregate().asString())
+		    .subscribe(s -> {
+		        result.set(s);
+		        responseReceivedLatch.countDown();
+		    });
+
+		assertThat(connectionOpenedLatch.await(30, TimeUnit.SECONDS)).isTrue();
+
+		// Stop accepting incoming requests, wait at most 1s for the active requests to finish
+		try {
+			this.disposableServer.channel()
+			                     .closeFuture()
+			                     .addListener(f -> delay.tryEmitValue("delay"));
+			// Reduce the timeout for testing purposes, by default it is 3s
+			this.disposableServer.disposeNow(Duration.ofSeconds(1));
+			fail("Expectation is that the socket cannot be closed");
+		}
+		catch (IllegalStateException e) {
+			// The socket couldn't be stopped, continue with shutdown
+			this.disposableServer = null;
+		}
+
+		// Reduce the quiet period and the timeout for testing purposes
+		// by default the quiet period is 2s and the timeout is 15s
+		loop.disposeLater(Duration.ofMillis(100), Duration.ofSeconds(1))
+		    .as(StepVerifier::create)
+		    .expectError(IllegalStateException.class)
+		    .verify(Duration.ofSeconds(5));
+
+		assertThat(connectionClosedLatch.await(30, TimeUnit.SECONDS)).isTrue();
+		assertThat(responseReceivedLatch.await(30, TimeUnit.SECONDS)).isTrue();
+		assertThat(result.get()).isNotNull().isEqualTo("delay");
+		stop.set(true);
+	}
+
 	@Test
 	void testHttpServerWithDomainSocketsNIOTransport() {
 		assertThatExceptionOfType(ChannelBindException.class)