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 0fc3b65d862..d349e3914cf 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
@@ -74,6 +74,7 @@ import org.springframework.context.aot.AotApplicationContextInitializer;
 import org.springframework.context.support.AbstractApplicationContext;
 import org.springframework.context.support.GenericApplicationContext;
 import org.springframework.core.GenericTypeResolver;
+import org.springframework.core.NativeDetector;
 import org.springframework.core.OrderComparator;
 import org.springframework.core.OrderComparator.OrderSourceProvider;
 import org.springframework.core.Ordered;
@@ -832,7 +833,16 @@ public class SpringApplication {
 			// Continue with normal handling of the original failure
 		}
 		if (logger.isErrorEnabled()) {
-			logger.error("Application run failed", failure);
+			if (NativeDetector.inNativeImage()) {
+				// Depending on how early the failure was, logging may not work in a
+				// native image so we output the stack trace directly to System.out
+				// instead.
+				System.out.println("Application run failed");
+				failure.printStackTrace(System.out);
+			}
+			else {
+				logger.error("Application run failed", failure);
+			}
 			registerLoggedException(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 68e65878a22..abf7d36c108 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
@@ -71,6 +71,7 @@ import org.springframework.boot.context.event.ApplicationStartedEvent;
 import org.springframework.boot.context.event.ApplicationStartingEvent;
 import org.springframework.boot.context.event.SpringApplicationEvent;
 import org.springframework.boot.convert.ApplicationConversionService;
+import org.springframework.boot.testsupport.classpath.ForkedClassPath;
 import org.springframework.boot.testsupport.system.CapturedOutput;
 import org.springframework.boot.testsupport.system.OutputCaptureExtension;
 import org.springframework.boot.web.embedded.netty.NettyReactiveWebServerFactory;
@@ -749,6 +750,53 @@ class SpringApplicationTests {
 		assertThat(output).contains("Application run failed");
 	}
 
+	@Test
+	void failureOnTheJvmLogsApplicationRunFailed(CapturedOutput output) {
+		SpringApplication application = new SpringApplication(ExampleConfig.class);
+		application.setWebApplicationType(WebApplicationType.NONE);
+		ExitCodeListener exitCodeListener = new ExitCodeListener();
+		application.addListeners(exitCodeListener);
+		@SuppressWarnings("unchecked")
+		ApplicationListener<SpringApplicationEvent> listener = mock(ApplicationListener.class);
+		application.addListeners(listener);
+		ExitStatusException failure = new ExitStatusException();
+		willThrow(failure).given(listener).onApplicationEvent(isA(ApplicationReadyEvent.class));
+		assertThatExceptionOfType(RuntimeException.class).isThrownBy(application::run);
+		then(listener).should().onApplicationEvent(isA(ApplicationReadyEvent.class));
+		then(listener).should(never()).onApplicationEvent(isA(ApplicationFailedEvent.class));
+		assertThat(exitCodeListener.getExitCode()).isEqualTo(11);
+		// Leading space only happens when logging
+		assertThat(output).contains(" Application run failed").contains("ExitStatusException");
+	}
+
+	@Test
+	@ForkedClassPath
+	void failureInANativeImageWritesFailureToSystemOut(CapturedOutput output) {
+		System.setProperty("org.graalvm.nativeimage.imagecode", "true");
+		try {
+			SpringApplication application = new SpringApplication(ExampleConfig.class);
+			application.setWebApplicationType(WebApplicationType.NONE);
+			ExitCodeListener exitCodeListener = new ExitCodeListener();
+			application.addListeners(exitCodeListener);
+			@SuppressWarnings("unchecked")
+			ApplicationListener<SpringApplicationEvent> listener = mock(ApplicationListener.class);
+			application.addListeners(listener);
+			ExitStatusException failure = new ExitStatusException();
+			willThrow(failure).given(listener).onApplicationEvent(isA(ApplicationReadyEvent.class));
+			assertThatExceptionOfType(RuntimeException.class).isThrownBy(application::run);
+			then(listener).should().onApplicationEvent(isA(ApplicationReadyEvent.class));
+			then(listener).should(never()).onApplicationEvent(isA(ApplicationFailedEvent.class));
+			assertThat(exitCodeListener.getExitCode()).isEqualTo(11);
+			// Leading space only happens when logging
+			assertThat(output).doesNotContain(" Application run failed")
+				.contains("Application run failed")
+				.contains("ExitStatusException");
+		}
+		finally {
+			System.clearProperty("org.graalvm.nativeimage.imagecode");
+		}
+	}
+
 	@Test
 	void loadSources() {
 		Class<?>[] sources = { ExampleConfig.class, TestCommandLineRunner.class };