diff --git a/servlet/src/main/java/io/undertow/servlet/core/DeploymentManagerImpl.java b/servlet/src/main/java/io/undertow/servlet/core/DeploymentManagerImpl.java
index 1a488d359c..d2e1bd8381 100644
--- a/servlet/src/main/java/io/undertow/servlet/core/DeploymentManagerImpl.java
+++ b/servlet/src/main/java/io/undertow/servlet/core/DeploymentManagerImpl.java
@@ -671,7 +671,7 @@ public void handleDeploymentSessionConfig(DeploymentInfo deploymentInfo, Servlet
 
     @Override
     public void undeploy() {
-        if(deployment.getDeploymentState() == State.DEPLOYED) {
+        if( deployment.getDeploymentState() == State.DEPLOYED || deployment.getDeploymentState() == State.STARTED) {
             //NOTE: this can happen if deployment isnt full and attempt is made to roll it back.
             try {
                 deployment.createThreadSetupAction(new ThreadSetupHandler.Action<Void, Object>() {
diff --git a/servlet/src/test/java/io/undertow/servlet/test/listener/servletcontext/ServletContextListenerTestCase2.java b/servlet/src/test/java/io/undertow/servlet/test/listener/servletcontext/ServletContextListenerTestCase2.java
new file mode 100644
index 0000000000..65d9982efa
--- /dev/null
+++ b/servlet/src/test/java/io/undertow/servlet/test/listener/servletcontext/ServletContextListenerTestCase2.java
@@ -0,0 +1,82 @@
+/*
+ * JBoss, Home of Professional Open Source.
+ * Copyright 2025 Red Hat, Inc., and individual contributors
+ * as indicated by the @author tags.
+ *
+ * Licensed 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.undertow.servlet.test.listener.servletcontext;
+
+import java.io.IOException;
+import java.util.Collections;
+
+import org.junit.Assert;
+import org.junit.BeforeClass;
+import org.junit.Test;
+import org.junit.runner.RunWith;
+
+import io.undertow.server.handlers.PathHandler;
+import io.undertow.servlet.api.DeploymentInfo;
+import io.undertow.servlet.api.DeploymentManager;
+import io.undertow.servlet.api.ListenerInfo;
+import io.undertow.servlet.api.ServletContainer;
+import io.undertow.servlet.api.ServletContainerInitializerInfo;
+import io.undertow.servlet.api.ServletInfo;
+import io.undertow.servlet.test.SimpleServletTestCase;
+import io.undertow.servlet.test.util.MessageServlet;
+import io.undertow.servlet.test.util.TestClassIntrospector;
+import io.undertow.testutils.DefaultServer;
+import jakarta.servlet.ServletException;
+
+/**
+ * @author Stuart Douglas
+ */
+@RunWith(DefaultServer.class)
+public class ServletContextListenerTestCase2 {
+
+    static DeploymentManager manager;
+
+    @BeforeClass
+    public static void setup() throws ServletException {
+
+        final PathHandler root = new PathHandler();
+        final ServletContainer container = ServletContainer.Factory.newInstance();
+
+        DeploymentInfo builder = new DeploymentInfo()
+                .setClassLoader(SimpleServletTestCase.class.getClassLoader())
+                .setContextPath("/servletContext")
+                .setClassIntrospecter(TestClassIntrospector.INSTANCE)
+                .setDeploymentName("servletContext.war")
+                .addServletContainerInitializer(new ServletContainerInitializerInfo(TestSci.class, Collections.<Class<?>>emptySet()))
+                .addServlet(
+                        new ServletInfo("servlet", MessageServlet.class)
+                                .addMapping("/aa")
+                )
+                .addListener(new ListenerInfo(ServletContextTestListener.class));
+
+
+        manager = container.addDeployment(builder);
+        manager.deploy();
+        root.addPrefixPath(builder.getContextPath(), manager.start());
+
+        DefaultServer.setRootHandler(root);
+    }
+
+    @Test
+    public void testServletContextDestroyed() throws IOException {
+        manager.undeploy();
+        Assert.assertNotNull(ServletContextTestListener.servletContextDestroyedEvent);
+    }
+
+}