diff --git a/spring-boot/src/main/java/org/springframework/boot/context/event/EventPublishingRunListener.java b/spring-boot/src/main/java/org/springframework/boot/context/event/EventPublishingRunListener.java
index 66ea0ed8db..1cd7c390e2 100644
--- a/spring-boot/src/main/java/org/springframework/boot/context/event/EventPublishingRunListener.java
+++ b/spring-boot/src/main/java/org/springframework/boot/context/event/EventPublishingRunListener.java
@@ -26,6 +26,7 @@ import org.springframework.context.ApplicationListener;
 import org.springframework.context.ConfigurableApplicationContext;
 import org.springframework.context.event.ApplicationEventMulticaster;
 import org.springframework.context.event.SimpleApplicationEventMulticaster;
+import org.springframework.context.support.AbstractApplicationContext;
 import org.springframework.core.Ordered;
 import org.springframework.core.env.ConfigurableEnvironment;
 import org.springframework.util.ErrorHandler;
@@ -93,12 +94,20 @@ public class EventPublishingRunListener implements SpringApplicationRunListener,
 	@Override
 	public void finished(ConfigurableApplicationContext context, Throwable exception) {
 		SpringApplicationEvent event = getFinishedEvent(context, exception);
-		if (context != null) {
+		if (context != null && context.isActive()) {
 			// Listeners have been registered to the application context so we should
 			// use it at this point if we can
 			context.publishEvent(event);
 		}
 		else {
+			// An inactive context may not have a multicaster so we use our multicaster to
+			// call all of the context's listeners instead
+			if (context instanceof AbstractApplicationContext) {
+				for (ApplicationListener<?> listener : ((AbstractApplicationContext) context)
+						.getApplicationListeners()) {
+					this.initialMulticaster.addApplicationListener(listener);
+				}
+			}
 			if (event instanceof ApplicationFailedEvent) {
 				this.initialMulticaster.setErrorHandler(new LoggingErrorHandler());
 			}
diff --git a/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java b/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
index c4bfd85237..83e7e48236 100644
--- a/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
+++ b/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
@@ -41,10 +41,12 @@ import reactor.core.publisher.Mono;
 
 import org.springframework.beans.BeansException;
 import org.springframework.beans.CachedIntrospectionResults;
+import org.springframework.beans.factory.BeanCreationException;
 import org.springframework.beans.factory.support.BeanDefinitionRegistry;
 import org.springframework.beans.factory.support.BeanNameGenerator;
 import org.springframework.beans.factory.support.DefaultBeanNameGenerator;
 import org.springframework.boot.context.event.ApplicationEnvironmentPreparedEvent;
+import org.springframework.boot.context.event.ApplicationFailedEvent;
 import org.springframework.boot.context.event.ApplicationPreparedEvent;
 import org.springframework.boot.context.event.ApplicationReadyEvent;
 import org.springframework.boot.context.event.ApplicationStartingEvent;
@@ -56,6 +58,7 @@ import org.springframework.boot.web.reactive.context.ReactiveWebServerApplicatio
 import org.springframework.boot.web.servlet.context.AnnotationConfigServletWebServerApplicationContext;
 import org.springframework.context.ApplicationContext;
 import org.springframework.context.ApplicationContextAware;
+import org.springframework.context.ApplicationContextException;
 import org.springframework.context.ApplicationContextInitializer;
 import org.springframework.context.ApplicationEvent;
 import org.springframework.context.ApplicationListener;
@@ -790,11 +793,92 @@ public class SpringApplicationTests {
 	private void verifyTestListenerEvents() {
 		ApplicationListener<ApplicationEvent> listener = this.context
 				.getBean("testApplicationListener", ApplicationListener.class);
-		verify(listener).onApplicationEvent(isA(ContextRefreshedEvent.class));
-		verify(listener).onApplicationEvent(isA(ApplicationReadyEvent.class));
+		verifyListenerEvents(listener, ContextRefreshedEvent.class,
+				ApplicationReadyEvent.class);
+	}
+
+	@SuppressWarnings("unchecked")
+	private void verifyListenerEvents(ApplicationListener<ApplicationEvent> listener,
+			Class<? extends ApplicationEvent>... eventTypes) {
+		for (Class<? extends ApplicationEvent> eventType : eventTypes) {
+			verify(listener).onApplicationEvent(isA(eventType));
+		}
 		verifyNoMoreInteractions(listener);
 	}
 
+	@SuppressWarnings("unchecked")
+	@Test
+	public void applicationListenerFromApplicationIsCalledWhenContextFailsRefreshBeforeListenerRegistration() {
+		ApplicationListener<ApplicationEvent> listener = mock(ApplicationListener.class);
+		SpringApplication application = new SpringApplication(ExampleConfig.class);
+		application.addListeners(listener);
+		try {
+			application.run();
+			fail("Run should have failed with an ApplicationContextException");
+		}
+		catch (ApplicationContextException ex) {
+			verifyListenerEvents(listener, ApplicationStartingEvent.class,
+					ApplicationEnvironmentPreparedEvent.class,
+					ApplicationPreparedEvent.class, ApplicationFailedEvent.class);
+		}
+	}
+
+	@SuppressWarnings("unchecked")
+	@Test
+	public void applicationListenerFromApplicationIsCalledWhenContextFailsRefreshAfterListenerRegistration() {
+		ApplicationListener<ApplicationEvent> listener = mock(ApplicationListener.class);
+		SpringApplication application = new SpringApplication(
+				BrokenPostConstructConfig.class);
+		application.setWebApplicationType(WebApplicationType.NONE);
+		application.addListeners(listener);
+		try {
+			application.run();
+			fail("Run should have failed with a BeanCreationException");
+		}
+		catch (BeanCreationException ex) {
+			verifyListenerEvents(listener, ApplicationStartingEvent.class,
+					ApplicationEnvironmentPreparedEvent.class,
+					ApplicationPreparedEvent.class, ApplicationFailedEvent.class);
+		}
+	}
+
+	@SuppressWarnings("unchecked")
+	@Test
+	public void applicationListenerFromContextIsCalledWhenContextFailsRefreshBeforeListenerRegistration() {
+		final ApplicationListener<ApplicationEvent> listener = mock(
+				ApplicationListener.class);
+		SpringApplication application = new SpringApplication(ExampleConfig.class);
+		application.addInitializers((applicationContext) -> {
+			applicationContext.addApplicationListener(listener);
+		});
+		try {
+			application.run();
+			fail("Run should have failed with an ApplicationContextException");
+		}
+		catch (ApplicationContextException ex) {
+			verifyListenerEvents(listener, ApplicationFailedEvent.class);
+		}
+	}
+
+	@SuppressWarnings("unchecked")
+	@Test
+	public void applicationListenerFromContextIsCalledWhenContextFailsRefreshAfterListenerRegistration() {
+		ApplicationListener<ApplicationEvent> listener = mock(ApplicationListener.class);
+		SpringApplication application = new SpringApplication(
+				BrokenPostConstructConfig.class);
+		application.setWebApplicationType(WebApplicationType.NONE);
+		application.addInitializers((applicationContext) -> {
+			applicationContext.addApplicationListener(listener);
+		});
+		try {
+			application.run();
+			fail("Run should have failed with a BeanCreationException");
+		}
+		catch (BeanCreationException ex) {
+			verifyListenerEvents(listener, ApplicationFailedEvent.class);
+		}
+	}
+
 	@Test
 	public void registerShutdownHookOff() throws Exception {
 		SpringApplication application = new SpringApplication(ExampleConfig.class);
@@ -1017,6 +1101,25 @@ public class SpringApplicationTests {
 
 	}
 
+	@Configuration
+	static class BrokenPostConstructConfig {
+
+		@Bean
+		public Thing thing() {
+			return new Thing();
+		}
+
+		static class Thing {
+
+			@PostConstruct
+			public void boom() {
+				throw new IllegalStateException();
+			}
+
+		}
+
+	}
+
 	@Configuration
 	static class ListenerConfig {