diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java
index 1c82413a1137..8caf83662d2e 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplication.java
@@ -786,6 +786,7 @@ private void handleRunFailure(ConfigurableApplicationContext context, Throwable
 				reportFailure(getExceptionReporters(context), exception);
 				if (context != null) {
 					context.close();
+					shutdownHook.deregisterFailedApplicationContext(context);
 				}
 			}
 		}
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplicationShutdownHook.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplicationShutdownHook.java
index 632688dd6354..debde8af7a59 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplicationShutdownHook.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/SpringApplicationShutdownHook.java
@@ -43,6 +43,7 @@
  *
  * @author Andy Wilkinson
  * @author Phillip Webb
+ * @author Brian Clozel
  */
 class SpringApplicationShutdownHook implements Runnable {
 
@@ -92,6 +93,17 @@ void addRuntimeShutdownHook() {
 		}
 	}
 
+	void deregisterFailedApplicationContext(ConfigurableApplicationContext applicationContext) {
+		synchronized (SpringApplicationShutdownHook.class) {
+			if (!applicationContext.isActive()) {
+				SpringApplicationShutdownHook.this.contexts.remove(applicationContext);
+			}
+			else {
+				throw new IllegalStateException("Cannot unregister active application context");
+			}
+		}
+	}
+
 	@Override
 	public void run() {
 		Set<ConfigurableApplicationContext> contexts;
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationShutdownHookTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationShutdownHookTests.java
index aed3d89ed255..2671b13e1ec3 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationShutdownHookTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationShutdownHookTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2021 the original author or authors.
+ * Copyright 2012-2022 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.
@@ -26,6 +26,7 @@
 import org.awaitility.Awaitility;
 import org.junit.jupiter.api.Test;
 
+import org.springframework.beans.factory.BeanCreationException;
 import org.springframework.beans.factory.InitializingBean;
 import org.springframework.beans.factory.config.ConfigurableListableBeanFactory;
 import org.springframework.beans.factory.support.DefaultListableBeanFactory;
@@ -36,12 +37,14 @@
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatIllegalArgumentException;
 import static org.assertj.core.api.Assertions.assertThatIllegalStateException;
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
 
 /**
  * Tests for {@link SpringApplicationShutdownHook}.
  *
  * @author Phillip Webb
  * @author Andy Wilkinson
+ * @author Brian Clozel
  */
 class SpringApplicationShutdownHookTests {
 
@@ -154,6 +157,29 @@ void removeHandlerActionWhenShuttingDownThrowsException() {
 				.withMessage("Shutdown in progress");
 	}
 
+	@Test
+	void failsWhenDeregisterActiveContext() {
+		TestSpringApplicationShutdownHook shutdownHook = new TestSpringApplicationShutdownHook();
+		ConfigurableApplicationContext context = new GenericApplicationContext();
+		shutdownHook.registerApplicationContext(context);
+		context.refresh();
+		assertThatThrownBy(() -> shutdownHook.deregisterFailedApplicationContext(context))
+				.isInstanceOf(IllegalStateException.class);
+		assertThat(shutdownHook.isApplicationContextRegistered(context)).isTrue();
+	}
+
+	@Test
+	void deregistersFailedContext() {
+		TestSpringApplicationShutdownHook shutdownHook = new TestSpringApplicationShutdownHook();
+		GenericApplicationContext context = new GenericApplicationContext();
+		shutdownHook.registerApplicationContext(context);
+		context.registerBean(FailingBean.class);
+		assertThatThrownBy(context::refresh).isInstanceOf(BeanCreationException.class);
+		assertThat(shutdownHook.isApplicationContextRegistered(context)).isTrue();
+		shutdownHook.deregisterFailedApplicationContext(context);
+		assertThat(shutdownHook.isApplicationContextRegistered(context)).isFalse();
+	}
+
 	static class TestSpringApplicationShutdownHook extends SpringApplicationShutdownHook {
 
 		private boolean runtimeShutdownHookAdded;
@@ -259,4 +285,13 @@ public void afterPropertiesSet() throws Exception {
 
 	}
 
+	static class FailingBean implements InitializingBean {
+
+		@Override
+		public void afterPropertiesSet() throws Exception {
+			throw new IllegalArgumentException("test failure");
+		}
+
+	}
+
 }
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
index 6a4d6e5c07ae..ffb1cff6f9b0 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/SpringApplicationTests.java
@@ -16,10 +16,12 @@
 
 package org.springframework.boot;
 
+import java.util.ArrayList;
 import java.util.Collections;
 import java.util.HashMap;
 import java.util.Iterator;
 import java.util.LinkedHashSet;
+import java.util.List;
 import java.util.Map;
 import java.util.Set;
 import java.util.concurrent.atomic.AtomicInteger;
@@ -150,6 +152,7 @@
  * @author Marten Deinum
  * @author Nguyen Bao Sach
  * @author Chris Bono
+ * @author Brian Clozel
  */
 @ExtendWith(OutputCaptureExtension.class)
 class SpringApplicationTests {
@@ -1247,6 +1250,20 @@ void bindsEnvironmentPrefixToSpringApplication() {
 		assertThat(application.getEnvironmentPrefix()).isEqualTo("my");
 	}
 
+	@Test
+	void deregistersShutdownHookForFailedApplicationContext() {
+		SpringApplication application = new SpringApplication(BrokenPostConstructConfig.class);
+		List<ApplicationEvent> events = new ArrayList<>();
+		application.addListeners(events::add);
+		application.setWebApplicationType(WebApplicationType.NONE);
+		assertThatExceptionOfType(BeanCreationException.class).isThrownBy(application::run);
+		assertThat(events).hasAtLeastOneElementOfType(ApplicationFailedEvent.class);
+		ApplicationFailedEvent failure = events.stream().filter((event) -> event instanceof ApplicationFailedEvent)
+				.map(ApplicationFailedEvent.class::cast).findFirst().get();
+		assertThat(SpringApplicationShutdownHookInstance.get())
+				.didNotRegisterApplicationContext(failure.getApplicationContext());
+	}
+
 	private <S extends AvailabilityState> ArgumentMatcher<ApplicationEvent> isAvailabilityChangeEventWithState(
 			S state) {
 		return (argument) -> (argument instanceof AvailabilityChangeEvent<?>)