diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/DeploymentManagerHttpHandlerFactory.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/DeploymentManagerHttpHandlerFactory.java
index 58bd09fcd70..46b9c71a902 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/DeploymentManagerHttpHandlerFactory.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/DeploymentManagerHttpHandlerFactory.java
@@ -22,6 +22,7 @@ import java.io.IOException;
 import io.undertow.server.HttpHandler;
 import io.undertow.server.HttpServerExchange;
 import io.undertow.servlet.api.DeploymentManager;
+import io.undertow.servlet.api.DeploymentManager.State;
 import jakarta.servlet.ServletException;
 
 import org.springframework.util.Assert;
@@ -76,12 +77,14 @@ class DeploymentManagerHttpHandlerFactory implements HttpHandlerFactory {
 
 		@Override
 		public void close() throws IOException {
-			try {
-				this.deploymentManager.stop();
-				this.deploymentManager.undeploy();
-			}
-			catch (ServletException ex) {
-				throw new RuntimeException(ex);
+			if (this.deploymentManager.getState() != State.UNDEPLOYED) {
+				try {
+					this.deploymentManager.stop();
+					this.deploymentManager.undeploy();
+				}
+				catch (ServletException ex) {
+					throw new RuntimeException(ex);
+				}
 			}
 		}
 
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServerFactoryTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServerFactoryTests.java
index 46cf2c3bcfe..79692703bf4 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServerFactoryTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/undertow/UndertowServletWebServerFactoryTests.java
@@ -54,6 +54,7 @@ import org.springframework.boot.web.server.ErrorPage;
 import org.springframework.boot.web.server.GracefulShutdownResult;
 import org.springframework.boot.web.server.PortInUseException;
 import org.springframework.boot.web.server.Shutdown;
+import org.springframework.boot.web.server.WebServer;
 import org.springframework.boot.web.servlet.ServletRegistrationBean;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactory;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactoryTests;
@@ -64,6 +65,7 @@ import org.springframework.test.util.ReflectionTestUtils;
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatIOException;
 import static org.assertj.core.api.Assertions.assertThatIllegalArgumentException;
+import static org.assertj.core.api.Assertions.assertThatNoException;
 import static org.hamcrest.Matchers.is;
 import static org.mockito.ArgumentMatchers.any;
 import static org.mockito.Mockito.inOrder;
@@ -320,6 +322,16 @@ class UndertowServletWebServerFactoryTests extends AbstractServletWebServerFacto
 			.isInstanceOfAny(SSLException.class, SocketException.class);
 	}
 
+	@Test
+	void multipleCallsToDestroyAreTolerated() {
+		AbstractServletWebServerFactory factory = getFactory();
+		factory.setPort(0);
+		WebServer webServer = factory.getWebServer();
+		webServer.start();
+		webServer.destroy();
+		assertThatNoException().isThrownBy(webServer::destroy);
+	}
+
 	@Override
 	protected JspServlet getJspServlet() {
 		return null; // Undertow does not support JSPs