I am not aware of anything like this @vkostyukov  @vkostyukov did you find out anything ? @normanmaurer Nope - we haven't really made any progress there yet. We've only seen this problem in our tests and were keeping an eye on complains coming from out users. Nobody really complained about slower shutdown yet thus we haven't really invested into it. k ok :) @vkostyukov would be interesting to know if #9616 resolves this (assuming it still happens for you). I think this should be fixed by #9616 . Closing. 
do we still need this sleep? 200ms seems a bit low, I see this failing on a loaded CI server. @johnou I think so yes since it's how the graceful shutdown / quiet period is currently implemented. That said polling with `sleep` for this does seem unnecessarily cumbersome (as hinted by the TODO comment above)... probably something for a follow-on improvement. Maybe it could be bumped a little, but 200ms seems to me like it should be long enough. The timeouts are intentionally low (< 1 sec) since that's what's currently needed to expose the underlying problem. As explained in the description the bug is largely "masked" by the 1sec default wait/select timeout.
Native epoll channels/sockets take longer to shutdown/close?
This is neither a bug report nor feature request. I figured I use Github issues to solicit peoples experience and knowledge about Netty's native epoll transports. We've been running Finagle with native epoll (on Linux) for quite a while internally and finally decided to switch our OSS version to it.

To our surprise, switching over to a native epoll caused out showdown tests to fail. Turns out, our previous graceful timeout (order of a couple of seconds) didn't do it for native epoll socket/channel (shutting down an HTTP server running with epoll=true). We had to bump our timeouts significantly to ensure the test passes: think of going from 2s to 30s.

Before we start digging into why closing epoll channels (server channels if that matters) takes so much longer I decided to ask around if somebody has seen this before. Any pointers would be totally appreciated!

I will try to post with thread with the updates should we know more.
common/src/main/java/io/netty/util/concurrent/SingleThreadEventExecutor.java
common/src/main/java/io/netty/util/concurrent/SingleThreadEventExecutor.java
testsuite/src/main/java/io/netty/testsuite/transport/AbstractSingleThreadEventLoopTest.java testsuite/src/main/java/io/netty/testsuite/transport/DefaultEventLoopTest.java testsuite/src/main/java/io/netty/testsuite/transport/NioEventLoopTest.java transport-native-epoll/src/test/java/io/netty/channel/epoll/EpollEventLoopTest.java transport-native-kqueue/src/test/java/io/netty/channel/kqueue/KQueueEventLoopTest.java transport/src/test/java/io/netty/channel/AbstractEventLoopTest.java
diff --git a/common/src/main/java/io/netty/util/concurrent/SingleThreadEventExecutor.java b/common/src/main/java/io/netty/util/concurrent/SingleThreadEventExecutor.java
index 4d77da11a73..d2b9707f393 100644
--- a/common/src/main/java/io/netty/util/concurrent/SingleThreadEventExecutor.java
+++ b/common/src/main/java/io/netty/util/concurrent/SingleThreadEventExecutor.java
@@ -587,7 +587,7 @@ protected void cleanup() {
     }
 
     protected void wakeup(boolean inEventLoop) {
-        if (!inEventLoop || state == ST_SHUTTING_DOWN) {
+        if (!inEventLoop) {
             // Use offer as we actually only need this to unblock the thread and if offer fails we do not care as there
             // is already something in the queue.
             taskQueue.offer(WAKEUP_TASK);
@@ -726,7 +726,10 @@ public Future<?> shutdownGracefully(long quietPeriod, long timeout, TimeUnit uni
         }
 
         if (wakeup) {
-            wakeup(inEventLoop);
+            taskQueue.offer(WAKEUP_TASK);
+            if (!addTaskWakesUp) {
+                wakeup(inEventLoop);
+            }
         }
 
         return terminationFuture();
@@ -778,7 +781,10 @@ public void shutdown() {
         }
 
         if (wakeup) {
-            wakeup(inEventLoop);
+            taskQueue.offer(WAKEUP_TASK);
+            if (!addTaskWakesUp) {
+                wakeup(inEventLoop);
+            }
         }
     }
 
@@ -827,7 +833,7 @@ protected boolean confirmShutdown() {
             if (gracefulShutdownQuietPeriod == 0) {
                 return true;
             }
-            wakeup(true);
+            taskQueue.offer(WAKEUP_TASK);
             return false;
         }
 
@@ -840,7 +846,7 @@ protected boolean confirmShutdown() {
         if (nanoTime - lastExecutionTime <= gracefulShutdownQuietPeriod) {
             // Check if any tasks were added to the queue every 100ms.
             // TODO: Change the behavior of takeTask() so that it returns on timeout.
-            wakeup(true);
+            taskQueue.offer(WAKEUP_TASK);
             try {
                 Thread.sleep(100);
             } catch (InterruptedException e) {

diff --git a/testsuite/src/main/java/io/netty/testsuite/transport/AbstractSingleThreadEventLoopTest.java b/testsuite/src/main/java/io/netty/testsuite/transport/AbstractSingleThreadEventLoopTest.java
index e4306b3dc8e..fd58a5255bc 100644
--- a/testsuite/src/main/java/io/netty/testsuite/transport/AbstractSingleThreadEventLoopTest.java
+++ b/testsuite/src/main/java/io/netty/testsuite/transport/AbstractSingleThreadEventLoopTest.java
@@ -15,14 +15,29 @@
  */
 package io.netty.testsuite.transport;
 
+import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertFalse;
+import static org.junit.Assert.assertTrue;
+import static org.junit.Assert.fail;
+
+import java.util.concurrent.CountDownLatch;
+import java.util.concurrent.RejectedExecutionException;
+import java.util.concurrent.TimeUnit;
+
 import org.junit.Test;
 
+import io.netty.bootstrap.ServerBootstrap;
 import io.netty.channel.Channel;
+import io.netty.channel.ChannelFuture;
+import io.netty.channel.ChannelInboundHandlerAdapter;
+import io.netty.channel.EventLoop;
 import io.netty.channel.EventLoopGroup;
+import io.netty.channel.ServerChannel;
 import io.netty.channel.SingleThreadEventLoop;
-import io.netty.channel.socket.ServerSocketChannel;
-
-import static org.junit.Assert.*;
+import io.netty.channel.local.LocalAddress;
+import io.netty.channel.local.LocalServerChannel;
+import io.netty.util.concurrent.EventExecutor;
+import io.netty.util.concurrent.Future;
 
 public abstract class AbstractSingleThreadEventLoopTest {
 
@@ -35,19 +50,108 @@ public void testChannelsRegistered()  {
             final Channel ch1 = newChannel();
             final Channel ch2 = newChannel();
 
-            assertEquals(0, loop.registeredChannels());
+            int rc = loop.registeredChannels();
+            boolean channelCountSupported = rc != -1;
+
+            if (channelCountSupported) {
+                assertEquals(0, loop.registeredChannels());
+            }
 
             assertTrue(loop.register(ch1).syncUninterruptibly().isSuccess());
             assertTrue(loop.register(ch2).syncUninterruptibly().isSuccess());
-            assertEquals(2, loop.registeredChannels());
+            if (channelCountSupported) {
+                assertEquals(2, loop.registeredChannels());
+            }
 
             assertTrue(ch1.deregister().syncUninterruptibly().isSuccess());
-            assertEquals(1, loop.registeredChannels());
+            if (channelCountSupported) {
+                assertEquals(1, loop.registeredChannels());
+            }
         } finally {
             group.shutdownGracefully();
         }
     }
 
+    @Test
+    @SuppressWarnings("deprecation")
+    public void shutdownBeforeStart() throws Exception {
+        EventLoopGroup group = newEventLoopGroup();
+        assertFalse(group.awaitTermination(2, TimeUnit.MILLISECONDS));
+        group.shutdown();
+        assertTrue(group.awaitTermination(200, TimeUnit.MILLISECONDS));
+    }
+
+    @Test
+    public void shutdownGracefullyZeroQuietBeforeStart() throws Exception {
+        EventLoopGroup group = newEventLoopGroup();
+        assertTrue(group.shutdownGracefully(0L, 2L, TimeUnit.SECONDS).await(200L));
+    }
+
+    // Copied from AbstractEventLoopTest
+    @Test(timeout = 5000)
+    public void testShutdownGracefullyNoQuietPeriod() throws Exception {
+        EventLoopGroup loop = newEventLoopGroup();
+        ServerBootstrap b = new ServerBootstrap();
+        b.group(loop)
+        .channel(serverChannelClass())
+        .childHandler(new ChannelInboundHandlerAdapter());
+
+        // Not close the Channel to ensure the EventLoop is still shutdown in time.
+        ChannelFuture cf = serverChannelClass() == LocalServerChannel.class
+                ? b.bind(new LocalAddress("local")) : b.bind(0);
+        cf.sync().channel();
+
+        Future<?> f = loop.shutdownGracefully(0, 1, TimeUnit.MINUTES);
+        assertTrue(loop.awaitTermination(600, TimeUnit.MILLISECONDS));
+        assertTrue(f.syncUninterruptibly().isSuccess());
+        assertTrue(loop.isShutdown());
+        assertTrue(loop.isTerminated());
+    }
+
+    @Test
+    public void shutdownGracefullyBeforeStart() throws Exception {
+        EventLoopGroup group = newEventLoopGroup();
+        assertTrue(group.shutdownGracefully(200L, 1000L, TimeUnit.MILLISECONDS).await(500L));
+    }
+
+    @Test
+    public void gracefulShutdownAfterStart() throws Exception {
+        EventLoop loop = newEventLoopGroup().next();
+        final CountDownLatch latch = new CountDownLatch(1);
+        loop.execute(new Runnable() {
+            @Override
+            public void run() {
+                latch.countDown();
+            }
+        });
+
+        // Wait for the event loop thread to start.
+        latch.await();
+
+        // Request the event loop thread to stop.
+        loop.shutdownGracefully(200L, 3000L, TimeUnit.MILLISECONDS);
+
+        // Wait until the event loop is terminated.
+        assertTrue(loop.awaitTermination(500L, TimeUnit.MILLISECONDS));
+
+        assertRejection(loop);
+    }
+
+    private static final Runnable NOOP = new Runnable() {
+        @Override
+        public void run() { }
+    };
+
+    private static void assertRejection(EventExecutor loop) {
+        try {
+            loop.execute(NOOP);
+            fail("A task must be rejected after shutdown() is called.");
+        } catch (RejectedExecutionException e) {
+            // Expected
+        }
+    }
+
     protected abstract EventLoopGroup newEventLoopGroup();
-    protected abstract ServerSocketChannel newChannel();
+    protected abstract Channel newChannel();
+    protected abstract Class<? extends ServerChannel> serverChannelClass();
 }
diff --git a/testsuite/src/main/java/io/netty/testsuite/transport/DefaultEventLoopTest.java b/testsuite/src/main/java/io/netty/testsuite/transport/DefaultEventLoopTest.java
new file mode 100644
index 00000000000..cb13b806241
--- /dev/null
+++ b/testsuite/src/main/java/io/netty/testsuite/transport/DefaultEventLoopTest.java
@@ -0,0 +1,41 @@
+/*
+ * Copyright 2019 The Netty Project
+ *
+ * The Netty Project licenses this file to you under the Apache License,
+ * version 2.0 (the "License"); you may not use this file except in compliance
+ * with the License. You may obtain a copy of the License at:
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS, WITHOUT
+ * WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
+ * License for the specific language governing permissions and limitations
+ * under the License.
+ */
+package io.netty.testsuite.transport;
+
+import io.netty.channel.Channel;
+import io.netty.channel.DefaultEventLoopGroup;
+import io.netty.channel.EventLoopGroup;
+import io.netty.channel.ServerChannel;
+import io.netty.channel.local.LocalChannel;
+import io.netty.channel.local.LocalServerChannel;
+
+public class DefaultEventLoopTest extends AbstractSingleThreadEventLoopTest {
+
+    @Override
+    protected EventLoopGroup newEventLoopGroup() {
+        return new DefaultEventLoopGroup();
+    }
+
+    @Override
+    protected Channel newChannel() {
+        return new LocalChannel();
+    }
+
+    @Override
+    protected Class<? extends ServerChannel> serverChannelClass() {
+        return LocalServerChannel.class;
+    }
+}
diff --git a/testsuite/src/main/java/io/netty/testsuite/transport/NioEventLoopTest.java b/testsuite/src/main/java/io/netty/testsuite/transport/NioEventLoopTest.java
new file mode 100644
index 00000000000..e4bc928907d
--- /dev/null
+++ b/testsuite/src/main/java/io/netty/testsuite/transport/NioEventLoopTest.java
@@ -0,0 +1,41 @@
+/*
+ * Copyright 2019 The Netty Project
+ *
+ * The Netty Project licenses this file to you under the Apache License,
+ * version 2.0 (the "License"); you may not use this file except in compliance
+ * with the License. You may obtain a copy of the License at:
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS, WITHOUT
+ * WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
+ * License for the specific language governing permissions and limitations
+ * under the License.
+ */
+package io.netty.testsuite.transport;
+
+import io.netty.channel.Channel;
+import io.netty.channel.EventLoopGroup;
+import io.netty.channel.ServerChannel;
+import io.netty.channel.nio.NioEventLoopGroup;
+import io.netty.channel.socket.nio.NioServerSocketChannel;
+import io.netty.channel.socket.nio.NioSocketChannel;
+
+public class NioEventLoopTest extends AbstractSingleThreadEventLoopTest {
+
+    @Override
+    protected EventLoopGroup newEventLoopGroup() {
+        return new NioEventLoopGroup();
+    }
+
+    @Override
+    protected Channel newChannel() {
+        return new NioSocketChannel();
+    }
+
+    @Override
+    protected Class<? extends ServerChannel> serverChannelClass() {
+        return NioServerSocketChannel.class;
+    }
+}
diff --git a/transport-native-epoll/src/test/java/io/netty/channel/epoll/EpollEventLoopTest.java b/transport-native-epoll/src/test/java/io/netty/channel/epoll/EpollEventLoopTest.java
index 0e057eb21a1..c6bc431d702 100644
--- a/transport-native-epoll/src/test/java/io/netty/channel/epoll/EpollEventLoopTest.java
+++ b/transport-native-epoll/src/test/java/io/netty/channel/epoll/EpollEventLoopTest.java
@@ -18,6 +18,7 @@
 import io.netty.channel.DefaultSelectStrategyFactory;
 import io.netty.channel.EventLoop;
 import io.netty.channel.EventLoopGroup;
+import io.netty.channel.ServerChannel;
 import io.netty.channel.socket.ServerSocketChannel;
 import io.netty.channel.unix.FileDescriptor;
 import io.netty.testsuite.transport.AbstractSingleThreadEventLoopTest;
@@ -49,6 +50,11 @@ protected ServerSocketChannel newChannel() {
         return new EpollServerSocketChannel();
     }
 
+    @Override
+    protected Class<? extends ServerChannel> serverChannelClass() {
+        return EpollServerSocketChannel.class;
+    }
+
     @Test
     public void testScheduleBigDelayNotOverflow() {
         final AtomicReference<Throwable> capture = new AtomicReference<Throwable>();
diff --git a/transport-native-kqueue/src/test/java/io/netty/channel/kqueue/KQueueEventLoopTest.java b/transport-native-kqueue/src/test/java/io/netty/channel/kqueue/KQueueEventLoopTest.java
index ceda867deaf..55d2e162a87 100644
--- a/transport-native-kqueue/src/test/java/io/netty/channel/kqueue/KQueueEventLoopTest.java
+++ b/transport-native-kqueue/src/test/java/io/netty/channel/kqueue/KQueueEventLoopTest.java
@@ -17,6 +17,7 @@
 
 import io.netty.channel.EventLoop;
 import io.netty.channel.EventLoopGroup;
+import io.netty.channel.ServerChannel;
 import io.netty.channel.socket.ServerSocketChannel;
 import io.netty.testsuite.transport.AbstractSingleThreadEventLoopTest;
 import io.netty.util.concurrent.Future;
@@ -39,6 +40,11 @@ protected ServerSocketChannel newChannel() {
         return new KQueueServerSocketChannel();
     }
 
+    @Override
+    protected Class<? extends ServerChannel> serverChannelClass() {
+        return KQueueServerSocketChannel.class;
+    }
+
     @Test
     public void testScheduleBigDelayNotOverflow() {
         EventLoopGroup group = new KQueueEventLoopGroup(1);
diff --git a/transport/src/test/java/io/netty/channel/AbstractEventLoopTest.java b/transport/src/test/java/io/netty/channel/AbstractEventLoopTest.java
index b4d29a67b66..df7fe13f869 100644
--- a/transport/src/test/java/io/netty/channel/AbstractEventLoopTest.java
+++ b/transport/src/test/java/io/netty/channel/AbstractEventLoopTest.java
@@ -75,7 +75,7 @@ public void testShutdownGracefullyNoQuietPeriod() throws Exception {
         b.bind(0).sync().channel();
 
         Future<?> f = loop.shutdownGracefully(0, 1, TimeUnit.MINUTES);
-        assertTrue(loop.awaitTermination(2, TimeUnit.SECONDS));
+        assertTrue(loop.awaitTermination(600, TimeUnit.MILLISECONDS));
         assertTrue(f.syncUninterruptibly().isSuccess());
         assertTrue(loop.isShutdown());
         assertTrue(loop.isTerminated());
