diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContext.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContext.java
index 9ff12bd8238d..8c787dd995aa 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContext.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContext.java
@@ -65,13 +65,18 @@ public final void refresh() throws BeansException, IllegalStateException {
 		try {
 			super.refresh();
 		}
-		catch (RuntimeException ex) {
+		catch (RuntimeException refreshEx) {
 			WebServer webServer = getWebServer();
 			if (webServer != null) {
-				webServer.stop();
-				webServer.destroy();
+				try {
+					webServer.stop();
+					webServer.destroy();
+				}
+				catch (RuntimeException stopOrDestroyEx) {
+					refreshEx.addSuppressed(stopOrDestroyEx);
+				}
 			}
-			throw ex;
+			throw refreshEx;
 		}
 	}
 
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContext.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContext.java
index 6562e68d1e8f..2555919b9572 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContext.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContext.java
@@ -145,13 +145,18 @@ public final void refresh() throws BeansException, IllegalStateException {
 		try {
 			super.refresh();
 		}
-		catch (RuntimeException ex) {
-			WebServer webServer = this.webServer;
-			if (webServer != null) {
-				webServer.stop();
-				webServer.destroy();
+		catch (RuntimeException refreshEx) {
+			try {
+				WebServer webServer = this.webServer;
+				if (webServer != null) {
+					webServer.stop();
+					webServer.destroy();
+				}
 			}
-			throw ex;
+			catch (RuntimeException stopOrDestroyEx) {
+				refreshEx.addSuppressed(stopOrDestroyEx);
+			}
+			throw refreshEx;
 		}
 	}
 
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContextTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContextTests.java
index e87deafa73ca..1c91af3fe14b 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContextTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/context/ReactiveWebServerApplicationContextTests.java
@@ -43,6 +43,7 @@
 import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
 import static org.assertj.core.api.Assertions.assertThatIllegalStateException;
 import static org.mockito.BDDMockito.then;
+import static org.mockito.BDDMockito.willThrow;
 import static org.mockito.Mockito.times;
 
 /**
@@ -133,6 +134,40 @@ void whenContextRefreshFailedThenWebServerIsStoppedAndDestroyed() {
 		then(webServer).should().destroy();
 	}
 
+	@Test
+	void whenContextRefreshFailedThenWebServerStopFailedCatchStopException() {
+		addWebServerFactoryBean();
+		addHttpHandlerBean();
+		this.context.registerBeanDefinition("refreshFailure", new RootBeanDefinition(RefreshFailure.class, () -> {
+			willThrow(new RuntimeException("WebServer has failed to stop")).willCallRealMethod()
+				.given(this.context.getWebServer())
+				.stop();
+			return new RefreshFailure();
+		}));
+		assertThatExceptionOfType(BeanCreationException.class).isThrownBy(this.context::refresh)
+			.withStackTraceContaining("WebServer has failed to stop");
+		WebServer webServer = this.context.getWebServer();
+		then(webServer).should().stop();
+		then(webServer).should(times(0)).destroy();
+	}
+
+	@Test
+	void whenContextRefreshFailedThenWebServerIsStoppedAndDestroyFailedCatchDestroyException() {
+		addWebServerFactoryBean();
+		addHttpHandlerBean();
+		this.context.registerBeanDefinition("refreshFailure", new RootBeanDefinition(RefreshFailure.class, () -> {
+			willThrow(new RuntimeException("WebServer has failed to destroy")).willCallRealMethod()
+				.given(this.context.getWebServer())
+				.destroy();
+			return new RefreshFailure();
+		}));
+		assertThatExceptionOfType(BeanCreationException.class).isThrownBy(this.context::refresh)
+			.withStackTraceContaining("WebServer has failed to destroy");
+		WebServer webServer = this.context.getWebServer();
+		then(webServer).should().stop();
+		then(webServer).should().destroy();
+	}
+
 	@Test
 	void whenContextIsClosedThenWebServerIsStoppedAndDestroyed() {
 		addWebServerFactoryBean();
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContextTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContextTests.java
index 694fb3828e4e..d474256bf607 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContextTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/context/ServletWebServerApplicationContextTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2024 the original author or authors.
+ * Copyright 2012-2025 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -51,6 +51,7 @@
 import org.springframework.boot.testsupport.system.CapturedOutput;
 import org.springframework.boot.testsupport.system.OutputCaptureExtension;
 import org.springframework.boot.web.context.ServerPortInfoApplicationContextInitializer;
+import org.springframework.boot.web.server.WebServer;
 import org.springframework.boot.web.servlet.DelegatingFilterProxyRegistrationBean;
 import org.springframework.boot.web.servlet.FilterRegistrationBean;
 import org.springframework.boot.web.servlet.ServletContextInitializer;
@@ -81,6 +82,7 @@
 import static org.mockito.ArgumentMatchers.anyString;
 import static org.mockito.BDDMockito.given;
 import static org.mockito.BDDMockito.then;
+import static org.mockito.BDDMockito.willThrow;
 import static org.mockito.Mockito.atMost;
 import static org.mockito.Mockito.inOrder;
 import static org.mockito.Mockito.mock;
@@ -211,6 +213,48 @@ void whenContextIsNotActiveThenCloseDoesNotChangeTheApplicationAvailability() {
 		assertThat(listener.receivedEvents()).isEmpty();
 	}
 
+	@Test
+	void whenContextRefreshFailedThenWebServerIsStoppedAndDestroyed() {
+		addWebServerFactoryBean();
+		this.context.registerBeanDefinition("refreshFailure", new RootBeanDefinition(RefreshFailure.class));
+		assertThatExceptionOfType(BeanCreationException.class).isThrownBy(this.context::refresh);
+		WebServer webServer = this.context.getWebServer();
+		then(webServer).should(times(2)).stop();
+		then(webServer).should().destroy();
+	}
+
+	@Test
+	void whenContextRefreshFailedThenWebServerStopFailedCatchStopException() {
+		addWebServerFactoryBean();
+		this.context.registerBeanDefinition("refreshFailure", new RootBeanDefinition(RefreshFailure.class, () -> {
+			willThrow(new RuntimeException("WebServer has failed to stop")).willCallRealMethod()
+				.given(this.context.getWebServer())
+				.stop();
+			return new RefreshFailure();
+		}));
+		assertThatExceptionOfType(BeanCreationException.class).isThrownBy(this.context::refresh)
+			.withStackTraceContaining("WebServer has failed to stop");
+		WebServer webServer = this.context.getWebServer();
+		then(webServer).should().stop();
+		then(webServer).should(times(0)).destroy();
+	}
+
+	@Test
+	void whenContextRefreshFailedThenWebServerIsStoppedAndDestroyFailedCatchDestroyException() {
+		addWebServerFactoryBean();
+		this.context.registerBeanDefinition("refreshFailure", new RootBeanDefinition(RefreshFailure.class, () -> {
+			willThrow(new RuntimeException("WebServer has failed to destroy")).willCallRealMethod()
+				.given(this.context.getWebServer())
+				.destroy();
+			return new RefreshFailure();
+		}));
+		assertThatExceptionOfType(BeanCreationException.class).isThrownBy(this.context::refresh)
+			.withStackTraceContaining("WebServer has failed to destroy");
+		WebServer webServer = this.context.getWebServer();
+		then(webServer).should().stop();
+		then(webServer).should().destroy();
+	}
+
 	@Test
 	void cannotSecondRefresh() {
 		addWebServerFactoryBean();