diff --git a/spring-test/src/main/java/org/springframework/test/context/BootstrapUtils.java b/spring-test/src/main/java/org/springframework/test/context/BootstrapUtils.java
index 2113cb0100e..19449b93454 100644
--- a/spring-test/src/main/java/org/springframework/test/context/BootstrapUtils.java
+++ b/spring-test/src/main/java/org/springframework/test/context/BootstrapUtils.java
@@ -19,15 +19,21 @@ package org.springframework.test.context;
 import java.lang.annotation.Annotation;
 import java.lang.reflect.Constructor;
 import java.util.LinkedHashSet;
+import java.util.Map;
 import java.util.Set;
+import java.util.TreeMap;
+import java.util.stream.Collectors;
 
 import org.apache.commons.logging.Log;
 import org.apache.commons.logging.LogFactory;
 import org.jspecify.annotations.Nullable;
 
 import org.springframework.beans.BeanUtils;
+import org.springframework.core.annotation.MergedAnnotation;
+import org.springframework.core.annotation.MergedAnnotationPredicates;
+import org.springframework.core.annotation.MergedAnnotations;
+import org.springframework.core.annotation.MergedAnnotations.SearchStrategy;
 import org.springframework.core.log.LogMessage;
-import org.springframework.test.context.TestContextAnnotationUtils.AnnotationDescriptor;
 import org.springframework.util.ClassUtils;
 
 /**
@@ -169,25 +175,33 @@ public abstract class BootstrapUtils {
 	}
 
 	private static @Nullable Class<?> resolveExplicitTestContextBootstrapper(Class<?> testClass) {
-		Set<BootstrapWith> annotations = new LinkedHashSet<>();
-		AnnotationDescriptor<BootstrapWith> descriptor =
-				TestContextAnnotationUtils.findAnnotationDescriptor(testClass, BootstrapWith.class);
-		while (descriptor != null) {
-			annotations.addAll(descriptor.findAllLocalMergedAnnotations());
-			descriptor = descriptor.next();
-		}
-
-		if (annotations.isEmpty()) {
+		Map<Integer, Set<BootstrapWith>> distanceToAnnotationsMap = MergedAnnotations.search(SearchStrategy.TYPE_HIERARCHY)
+				.withEnclosingClasses(TestContextAnnotationUtils::searchEnclosingClass)
+				.from(testClass)
+				.stream(BootstrapWith.class)
+				// The following effectively filters out annotations in the type and
+				// enclosing class hierarchies once annotations have already been found
+				// on a particular class or interface.
+				.filter(MergedAnnotationPredicates.firstRunOf(MergedAnnotation::getAggregateIndex))
+				// Grouping by "meta-distance" enables us to allow a directly-present
+				// annotation to override annotations that are meta-present.
+				// Collecting synthesized annotations for each meta-distance enables
+				// us to filter out duplicates.
+				.collect(Collectors.groupingBy(MergedAnnotation::getDistance, TreeMap::new,
+						Collectors.mapping(MergedAnnotation::synthesize, Collectors.toCollection(LinkedHashSet::new))));
+
+		if (distanceToAnnotationsMap.isEmpty()) {
 			return null;
 		}
-		if (annotations.size() == 1) {
-			return annotations.iterator().next().value();
-		}
 
-		// Allow directly-present annotation to override annotations that are meta-present.
-		BootstrapWith bootstrapWith = testClass.getDeclaredAnnotation(BootstrapWith.class);
-		if (bootstrapWith != null) {
-			return bootstrapWith.value();
+		Set<BootstrapWith> annotations = new LinkedHashSet<>();
+		for (Set<BootstrapWith> currentAnnotations: distanceToAnnotationsMap.values()) {
+			// If we have found a single, non-competing @BootstrapWith annotation, return it.
+			if (annotations.isEmpty() && currentAnnotations.size() == 1) {
+				return currentAnnotations.iterator().next().value();
+			}
+			// Otherwise, track all discovered annotations for error reporting.
+			annotations.addAll(currentAnnotations);
 		}
 
 		throw new IllegalStateException(String.format(
diff --git a/spring-test/src/test/java/org/springframework/test/context/BootstrapUtilsTests.java b/spring-test/src/test/java/org/springframework/test/context/BootstrapUtilsTests.java
index 6d9077ec6ae..fff6c5f3a4b 100644
--- a/spring-test/src/test/java/org/springframework/test/context/BootstrapUtilsTests.java
+++ b/spring-test/src/test/java/org/springframework/test/context/BootstrapUtilsTests.java
@@ -146,13 +146,7 @@ class BootstrapUtilsTests {
 	 */
 	@Test  // gh-35938
 	void resolveTestContextBootstrapperWithMetaBootstrapWithAnnotationThatOverridesMetaMetaBootstrapWithAnnotation() {
-		BootstrapContext bootstrapContext = BootstrapTestUtils.buildBootstrapContext(
-				MetaAndMetaMetaBootstrapWithAnnotationsClass.class, delegate);
-			assertThatIllegalStateException()
-				.isThrownBy(() -> resolveTestContextBootstrapper(bootstrapContext))
-				.withMessageContaining("Configuration error: found multiple declarations of @BootstrapWith")
-				.withMessageContaining(FooBootstrapper.class.getSimpleName())
-				.withMessageContaining(BarBootstrapper.class.getSimpleName());
+		assertBootstrapper(MetaAndMetaMetaBootstrapWithAnnotationsClass.class, BarBootstrapper.class);
 	}
 
 	/**