diff --git a/jetty-io/src/main/java/org/eclipse/jetty/io/SelectorManager.java b/jetty-io/src/main/java/org/eclipse/jetty/io/SelectorManager.java
index 97195afe488..f14c3b950b4 100644
--- a/jetty-io/src/main/java/org/eclipse/jetty/io/SelectorManager.java
+++ b/jetty-io/src/main/java/org/eclipse/jetty/io/SelectorManager.java
@@ -748,14 +748,30 @@ public abstract class SelectorManager extends AbstractLifeCycle implements Dumpa
                 }
                 catch (ClosedSelectorException | ClosedChannelException x)
                 {
-                    LOG.debug(x);
+                    failed(x);
                 }
             }
 
             protected void failed(Throwable failure)
             {
                 if (failed.compareAndSet(false, true))
+                {
+                    timeout.cancel();
+                    close();
                     connectionFailed(channel, failure, attachment);
+                }
+            }
+
+            private void close()
+            {
+                try
+                {
+                    channel.close();
+                }
+                catch (IOException x)
+                {
+                    LOG.ignore(x);
+                }
             }
         }
 
@@ -775,19 +791,7 @@ public abstract class SelectorManager extends AbstractLifeCycle implements Dumpa
                 if (channel.isConnectionPending())
                 {
                     LOG.debug("Channel {} timed out while connecting, closing it", channel);
-                    try
-                    {
-                        // This will unregister the channel from the selector
-                        channel.close();
-                    }
-                    catch (IOException x)
-                    {
-                        LOG.ignore(x);
-                    }
-                    finally
-                    {
-                        connect.failed(new SocketTimeoutException());
-                    }
+                    connect.failed(new SocketTimeoutException());
                 }
             }
         }
diff --git a/jetty-io/src/test/java/org/eclipse/jetty/io/SelectorManagerTest.java b/jetty-io/src/test/java/org/eclipse/jetty/io/SelectorManagerTest.java
index 4167a2dd079..f1710652910 100644
--- a/jetty-io/src/test/java/org/eclipse/jetty/io/SelectorManagerTest.java
+++ b/jetty-io/src/test/java/org/eclipse/jetty/io/SelectorManagerTest.java
@@ -26,6 +26,7 @@ import java.nio.channels.ServerSocketChannel;
 import java.nio.channels.SocketChannel;
 import java.util.concurrent.CountDownLatch;
 import java.util.concurrent.TimeUnit;
+import java.util.concurrent.atomic.AtomicBoolean;
 
 import org.eclipse.jetty.toolchain.test.annotation.Slow;
 import org.eclipse.jetty.util.Callback;
@@ -67,6 +68,7 @@ public class SelectorManagerTest
         client.configureBlocking(false);
         client.connect(address);
 
+        final AtomicBoolean timeoutConnection = new AtomicBoolean();
         final long connectTimeout = 1000;
         SelectorManager selectorManager = new SelectorManager(executor, scheduler)
         {
@@ -81,7 +83,8 @@ public class SelectorManagerTest
             {
                 try
                 {
-                    TimeUnit.MILLISECONDS.sleep(connectTimeout * 2);
+                    if (timeoutConnection.get())
+                        TimeUnit.MILLISECONDS.sleep(connectTimeout * 2);
                     return super.finishConnect(channel);
                 }
                 catch (InterruptedException e)
@@ -113,17 +116,30 @@ public class SelectorManagerTest
 
         try
         {
-            final CountDownLatch latch = new CountDownLatch(1);
+            timeoutConnection.set(true);
+            final CountDownLatch latch1 = new CountDownLatch(1);
             selectorManager.connect(client, new Callback.Adapter()
             {
                 @Override
                 public void failed(Throwable x)
                 {
-                    latch.countDown();
+                    latch1.countDown();
                 }
             });
+            Assert.assertTrue(latch1.await(connectTimeout * 3, TimeUnit.MILLISECONDS));
 
-            Assert.assertTrue(latch.await(connectTimeout * 3, TimeUnit.MILLISECONDS));
+            // Verify that after the failure we can connect successfully
+            timeoutConnection.set(false);
+            final CountDownLatch latch2 = new CountDownLatch(1);
+            selectorManager.connect(client, new Callback.Adapter()
+            {
+                @Override
+                public void failed(Throwable x)
+                {
+                    latch2.countDown();
+                }
+            });
+            Assert.assertTrue(latch2.await(connectTimeout, TimeUnit.MILLISECONDS));
         }
         finally
         {