diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/AotInitializerNotFoundException.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/AotInitializerNotFoundException.java
new file mode 100644
index 0000000000..1bd8d4f6fc
--- /dev/null
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/AotInitializerNotFoundException.java
@@ -0,0 +1,39 @@
+/*
+ * Copyright 2012-2024 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.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot;
+
+/**
+ * Exception thrown when the AOT initializer couldn't be found.
+ *
+ * @author Moritz Halbritter
+ * @since 3.2.6
+ */
+public class AotInitializerNotFoundException extends RuntimeException {
+
+	private final Class<?> mainClass;
+
+	public AotInitializerNotFoundException(Class<?> mainClass, String initializerClassName) {
+		super("Startup with AOT mode enabled failed: AOT initializer %s could not be found"
+			.formatted(initializerClassName));
+		this.mainClass = mainClass;
+	}
+
+	public Class<?> getMainClass() {
+		return this.mainClass;
+	}
+
+}
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 01277d0dfb..480d9a94d3 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
@@ -439,10 +439,9 @@ public class SpringApplication {
 					initializers.stream().filter(AotApplicationContextInitializer.class::isInstance).toList());
 			if (aotInitializers.isEmpty()) {
 				String initializerClassName = this.mainApplicationClass.getName() + "__ApplicationContextInitializer";
-				Assert.state(ClassUtils.isPresent(initializerClassName, getClassLoader()),
-						"You are starting the application with AOT mode enabled but AOT processing hasn't happened. "
-								+ "Please build your application with enabled AOT processing first, "
-								+ "or remove the system property 'spring.aot.enabled' to run the application in regular mode");
+				if (!ClassUtils.isPresent(initializerClassName, getClassLoader())) {
+					throw new AotInitializerNotFoundException(this.mainApplicationClass, initializerClassName);
+				}
 				aotInitializers.add(AotApplicationContextInitializer.forInitializerClasses(initializerClassName));
 			}
 			initializers.removeAll(aotInitializers);
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/diagnostics/analyzer/AotInitializerNotFoundFailureAnalyzer.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/diagnostics/analyzer/AotInitializerNotFoundFailureAnalyzer.java
new file mode 100644
index 0000000000..ac3db4fdf4
--- /dev/null
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/diagnostics/analyzer/AotInitializerNotFoundFailureAnalyzer.java
@@ -0,0 +1,40 @@
+/*
+ * Copyright 2012-2024 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.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.diagnostics.analyzer;
+
+import org.springframework.boot.AotInitializerNotFoundException;
+import org.springframework.boot.diagnostics.AbstractFailureAnalyzer;
+import org.springframework.boot.diagnostics.FailureAnalysis;
+
+/**
+ * An {@link AbstractFailureAnalyzer} that performs analysis of failures caused by a
+ * {@link AotInitializerNotFoundException}.
+ *
+ * @author Moritz Halbritter
+ */
+class AotInitializerNotFoundFailureAnalyzer extends AbstractFailureAnalyzer<AotInitializerNotFoundException> {
+
+	@Override
+	protected FailureAnalysis analyze(Throwable rootFailure, AotInitializerNotFoundException cause) {
+		return new FailureAnalysis(cause.getMessage(), "Consider the following:\n"
+				+ "\tDid you build the application with enabled AOT processing?\n"
+				+ "\tIs the main class %s correct?\n".formatted(cause.getMainClass().getName())
+				+ "\tIf you want to run the application in regular mode, remove the system property 'spring.aot.enabled'",
+				cause);
+	}
+
+}
diff --git a/spring-boot-project/spring-boot/src/main/resources/META-INF/spring.factories b/spring-boot-project/spring-boot/src/main/resources/META-INF/spring.factories
index f6cea1c9e6..18bbe901ab 100644
--- a/spring-boot-project/spring-boot/src/main/resources/META-INF/spring.factories
+++ b/spring-boot-project/spring-boot/src/main/resources/META-INF/spring.factories
@@ -64,6 +64,7 @@ org.springframework.boot.diagnostics.FailureAnalyzer=\
 org.springframework.boot.context.config.ConfigDataNotFoundFailureAnalyzer,\
 org.springframework.boot.context.properties.IncompatibleConfigurationFailureAnalyzer,\
 org.springframework.boot.context.properties.NotConstructorBoundInjectionFailureAnalyzer,\
+org.springframework.boot.diagnostics.analyzer.AotInitializerNotFoundFailureAnalyzer,\
 org.springframework.boot.diagnostics.analyzer.BeanCurrentlyInCreationFailureAnalyzer,\
 org.springframework.boot.diagnostics.analyzer.BeanDefinitionOverrideFailureAnalyzer,\
 org.springframework.boot.diagnostics.analyzer.BeanNotOfRequiredTypeFailureAnalyzer,\
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 e6b2e72f4e..0bce832b57 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
@@ -1445,8 +1445,8 @@ class SpringApplicationTests {
 		application.setMainApplicationClass(TestSpringApplication.class);
 		System.setProperty(AotDetector.AOT_ENABLED, "true");
 		try {
-			assertThatIllegalStateException().isThrownBy(application::run)
-				.withMessageContaining("but AOT processing hasn't happened");
+			assertThatExceptionOfType(AotInitializerNotFoundException.class).isThrownBy(application::run)
+				.withMessageMatching("^.+AOT initializer .+ could not be found$");
 		}
 		finally {
 			System.clearProperty(AotDetector.AOT_ENABLED);
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/diagnostics/analyzer/AotInitializerNotFoundFailureAnalyzerTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/diagnostics/analyzer/AotInitializerNotFoundFailureAnalyzerTests.java
new file mode 100644
index 0000000000..500e516f1e
--- /dev/null
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/diagnostics/analyzer/AotInitializerNotFoundFailureAnalyzerTests.java
@@ -0,0 +1,52 @@
+/*
+ * Copyright 2012-2024 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.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.diagnostics.analyzer;
+
+import org.junit.jupiter.api.Test;
+
+import org.springframework.boot.AotInitializerNotFoundException;
+import org.springframework.boot.diagnostics.FailureAnalysis;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * Tests for {@link AotInitializerNotFoundFailureAnalyzer}.
+ *
+ * @author Moritz Halbritter
+ */
+class AotInitializerNotFoundFailureAnalyzerTests {
+
+	@Test
+	void shouldAnalyze() {
+		FailureAnalysis analysis = analyze();
+		assertThat(analysis.getDescription()).isEqualTo(
+				"Startup with AOT mode enabled failed: AOT initializer class org.springframework.boot.diagnostics.analyzer.AotInitializerNotFoundFailureAnalyzerTests__ApplicationContextInitializer could not be found");
+		assertThat(analysis.getAction()).isEqualTo(
+				"""
+						Consider the following:
+						\tDid you build the application with enabled AOT processing?
+						\tIs the main class org.springframework.boot.diagnostics.analyzer.AotInitializerNotFoundFailureAnalyzerTests correct?
+						\tIf you want to run the application in regular mode, remove the system property 'spring.aot.enabled'""");
+	}
+
+	private FailureAnalysis analyze() {
+		return new AotInitializerNotFoundFailureAnalyzer()
+			.analyze(new AotInitializerNotFoundException(AotInitializerNotFoundFailureAnalyzerTests.class,
+					AotInitializerNotFoundFailureAnalyzerTests.class + "__ApplicationContextInitializer"));
+	}
+
+}