diff --git a/spring-core/src/main/java/org/springframework/aot/hint/support/RuntimeHintsUtils.java b/spring-core/src/main/java/org/springframework/aot/hint/support/RuntimeHintsUtils.java
index b8eff9c103f..a859807883d 100644
--- a/spring-core/src/main/java/org/springframework/aot/hint/support/RuntimeHintsUtils.java
+++ b/spring-core/src/main/java/org/springframework/aot/hint/support/RuntimeHintsUtils.java
@@ -60,7 +60,10 @@ public abstract class RuntimeHintsUtils {
 		hints.reflection().registerType(annotationType, ANNOTATION_HINT);
 		Set<Class<?>> allAnnotations = new LinkedHashSet<>();
 		collectAliasedAnnotations(new HashSet<>(), allAnnotations, annotationType);
-		allAnnotations.forEach(annotation -> hints.reflection().registerType(annotation, ANNOTATION_HINT));
+		allAnnotations.forEach(annotation -> {
+			hints.reflection().registerType(annotation, ANNOTATION_HINT);
+			hints.proxies().registerJdkProxy(annotation, SynthesizedAnnotation.class);
+		});
 		if (!allAnnotations.isEmpty()) {
 			hints.proxies().registerJdkProxy(annotationType, SynthesizedAnnotation.class);
 		}
diff --git a/spring-core/src/test/java/org/springframework/aot/hint/support/RuntimeHintsUtilsTests.java b/spring-core/src/test/java/org/springframework/aot/hint/support/RuntimeHintsUtilsTests.java
index 5a7464040c0..385a2c951bb 100644
--- a/spring-core/src/test/java/org/springframework/aot/hint/support/RuntimeHintsUtilsTests.java
+++ b/spring-core/src/test/java/org/springframework/aot/hint/support/RuntimeHintsUtilsTests.java
@@ -60,13 +60,15 @@ class RuntimeHintsUtilsTests {
 	}
 
 	@Test
-	void registerAnnotationTypeProxyRegistersJdkProxy() {
+	void registerAnnotationTypeProxyRegistersJdkProxies() {
 		RuntimeHintsUtils.registerAnnotation(this.hints, RetryInvoker.class);
 		assertThat(this.hints.reflection().typeHints())
 				.anySatisfy(annotationHint(RetryInvoker.class))
 				.anySatisfy(annotationHint(SampleInvoker.class));
-		assertThat(this.hints.proxies().jdkProxies()).singleElement()
-				.satisfies(annotationProxy(RetryInvoker.class));
+		assertThat(this.hints.proxies().jdkProxies())
+				.anySatisfy(annotationProxy(RetryInvoker.class))
+				.anySatisfy(annotationProxy(SampleInvoker.class))
+				.hasSize(2);
 	}
 
 	@Test
@@ -78,8 +80,11 @@ class RuntimeHintsUtilsTests {
 				.anySatisfy(annotationHint(RetryInvoker.class))
 				.anySatisfy(annotationHint(SampleInvoker.class))
 				.hasSize(3);
-		assertThat(this.hints.proxies().jdkProxies()).singleElement()
-				.satisfies(annotationProxy(RetryWithEnabledFlagInvoker.class));
+		assertThat(this.hints.proxies().jdkProxies())
+				.anySatisfy(annotationProxy(RetryWithEnabledFlagInvoker.class))
+				.anySatisfy(annotationProxy(RetryInvoker.class))
+				.anySatisfy(annotationProxy(SampleInvoker.class))
+				.hasSize(3);
 	}
 
 	private Consumer<TypeHint> annotationHint(Class<?> type) {