diff --git a/core/src/main/java/de/bwaldvogel/mongo/MongoServer.java b/core/src/main/java/de/bwaldvogel/mongo/MongoServer.java
index cd3065af..644e3c6d 100644
--- a/core/src/main/java/de/bwaldvogel/mongo/MongoServer.java
+++ b/core/src/main/java/de/bwaldvogel/mongo/MongoServer.java
@@ -181,6 +181,10 @@ public void shutdown() {
             workerGroup.terminationFuture().syncUninterruptibly();
         }
 
+        // A client that connected while the event loops were shutting down can still be in the group, but its event
+        // loop has terminated and would never complete closing it. A later shutdownNow() must not wait for that.
+        channelGroup = null;
+
         backend.close();
 
         log.info("completed shutdown of {}", this);
diff --git a/core/src/test/java/de/bwaldvogel/mongo/MongoServerShutdownTest.java b/core/src/test/java/de/bwaldvogel/mongo/MongoServerShutdownTest.java
new file mode 100644
index 00000000..b59aa936
--- /dev/null
+++ b/core/src/test/java/de/bwaldvogel/mongo/MongoServerShutdownTest.java
@@ -0,0 +1,90 @@
+package de.bwaldvogel.mongo;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.junit.jupiter.api.Assertions.assertTimeoutPreemptively;
+import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.Mockito.doAnswer;
+import static org.mockito.Mockito.mock;
+
+import java.net.InetSocketAddress;
+import java.net.Socket;
+import java.time.Duration;
+import java.util.concurrent.CountDownLatch;
+import java.util.concurrent.TimeUnit;
+import java.util.function.BooleanSupplier;
+
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.Timeout;
+
+import io.netty.channel.Channel;
+import io.netty.util.concurrent.SingleThreadEventExecutor;
+
+class MongoServerShutdownTest {
+
+    private static final int TIMEOUT_SECONDS = 10;
+
+    @Test
+    @Timeout(3 * TIMEOUT_SECONDS)
+    void testShutdownNowAfterClientConnectedDuringShutdown() throws Exception {
+        CountDownLatch workerHeld = new CountDownLatch(1);
+        CountDownLatch secondClientQueued = new CountDownLatch(1);
+
+        MongoBackend backend = mock(MongoBackend.class);
+        doAnswer(invocation -> {
+            if (workerHeld.getCount() > 0) {
+                holdWorker(invocation.getArgument(0), workerHeld, secondClientQueued);
+            }
+            return null;
+        }).when(backend).handleClose(any());
+
+        MongoServer server = new MongoServer(backend);
+        try {
+            // a single worker thread, so that the second client is registered only after the first client's close
+            server.bind(new InetSocketAddress("localhost", 0), 1, 1);
+            InetSocketAddress address = server.getLocalAddress();
+
+            new Socket(address.getHostString(), address.getPort()).close();
+            assertThat(workerHeld.await(TIMEOUT_SECONDS, TimeUnit.SECONDS)).isTrue();
+
+            try (Socket secondClient = new Socket(address.getHostString(), address.getPort())) {
+                assertThat(secondClientQueued.await(TIMEOUT_SECONDS, TimeUnit.SECONDS)).isTrue();
+
+                // the second client is registered after its event loop started to shut down, and stays open
+                server.shutdownNow();
+
+                assertTimeoutPreemptively(Duration.ofSeconds(TIMEOUT_SECONDS), server::shutdownNow);
+            }
+        } finally {
+            server.shutdown();
+        }
+    }
+
+    /**
+     * Keeps the only worker thread in the first client's close until the second client's registration is queued
+     * behind it and the server has started to shut down.
+     */
+    private static void holdWorker(Channel channel, CountDownLatch workerHeld, CountDownLatch secondClientQueued) {
+        SingleThreadEventExecutor worker = (SingleThreadEventExecutor) channel.eventLoop();
+        int pendingTasks = worker.pendingTasks();
+        workerHeld.countDown();
+        awaitCondition(() -> worker.pendingTasks() > pendingTasks);
+        secondClientQueued.countDown();
+        awaitCondition(worker::isShuttingDown);
+    }
+
+    private static void awaitCondition(BooleanSupplier condition) {
+        long deadline = System.nanoTime() + TimeUnit.SECONDS.toNanos(TIMEOUT_SECONDS);
+        while (!condition.getAsBoolean()) {
+            if (System.nanoTime() > deadline) {
+                throw new IllegalStateException("Condition not met within " + TIMEOUT_SECONDS + " seconds");
+            }
+            try {
+                Thread.sleep(1);
+            } catch (InterruptedException e) {
+                Thread.currentThread().interrupt();
+                throw new IllegalStateException(e);
+            }
+        }
+    }
+
+}