diff --git a/test/src/main/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListener.java b/test/src/main/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListener.java
index 3cc8a505d3..5e6328dc49 100644
--- a/test/src/main/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListener.java
+++ b/test/src/main/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListener.java
@@ -71,7 +71,7 @@ public class WithSecurityContextTestExecutionListener extends
 		if (withSecurityContext != null) {
 			WithSecurityContextFactory factory = createFactory(withSecurityContext, context);
 			Class<? extends Annotation> type = (Class<? extends Annotation>) GenericTypeResolver.resolveTypeArgument(factory.getClass(), WithSecurityContextFactory.class);
-			Annotation annotation  = AnnotationUtils.findAnnotation(annotated, type);
+			Annotation annotation = findAnnotation(annotated, type);
 			try {
 				return factory.createSecurityContext(annotation);
 			}
@@ -83,6 +83,23 @@ public class WithSecurityContextTestExecutionListener extends
 		return null;
 	}
 
+	private Annotation findAnnotation(AnnotatedElement annotated,
+			Class<? extends Annotation> type) {
+		Annotation findAnnotation = AnnotationUtils.findAnnotation(annotated, type);
+		if (findAnnotation != null) {
+			return findAnnotation;
+		}
+		Annotation[] allAnnotations = AnnotationUtils.getAnnotations(annotated);
+		for (Annotation annotationToTest : allAnnotations) {
+			WithSecurityContext withSecurityContext = AnnotationUtils.findAnnotation(
+					annotationToTest.annotationType(), WithSecurityContext.class);
+			if (withSecurityContext != null) {
+				return annotationToTest;
+			}
+		}
+		return null;
+	}
+
 	private WithSecurityContextFactory<? extends Annotation> createFactory(
 			WithSecurityContext withSecurityContext, TestContext testContext) {
 		Class<? extends WithSecurityContextFactory<? extends Annotation>> clazz = withSecurityContext
diff --git a/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListenerTests.java b/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListenerTests.java
index 029b860401..a468115321 100644
--- a/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListenerTests.java
+++ b/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExecutionListenerTests.java
@@ -15,16 +15,29 @@
  */
 package org.springframework.security.test.context.support;
 
-import static org.assertj.core.api.Assertions.*;
-
+import java.lang.annotation.Annotation;
+import java.lang.annotation.Retention;
+import java.lang.annotation.RetentionPolicy;
+import java.lang.reflect.Method;
 import java.util.ArrayList;
 import java.util.List;
 
+import org.junit.After;
 import org.junit.Before;
 import org.junit.Test;
+
 import org.springframework.core.annotation.AnnotationAwareOrderComparator;
+import org.springframework.security.authentication.TestingAuthenticationToken;
+import org.springframework.security.core.context.SecurityContext;
+import org.springframework.security.core.context.SecurityContextHolder;
+import org.springframework.test.context.TestContext;
 import org.springframework.test.context.TestExecutionListener;
 import org.springframework.test.context.support.DependencyInjectionTestExecutionListener;
+import org.springframework.util.ReflectionUtils;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.when;
 
 /**
  * @author Rob Winch
@@ -35,7 +48,12 @@ public class WithSecurityContextTestExecutionListenerTests {
 
 	@Before
 	public void setup() {
-		listener = new WithSecurityContextTestExecutionListener();
+		this.listener = new WithSecurityContextTestExecutionListener();
+	}
+
+	@After
+	public void cleanup() {
+		SecurityContextHolder.clearContext();
 	}
 
 	// SEC-2709
@@ -45,10 +63,48 @@ public class WithSecurityContextTestExecutionListenerTests {
 
 		List<TestExecutionListener> listeners = new ArrayList<TestExecutionListener>();
 		listeners.add(otherListener);
-		listeners.add(listener);
+		listeners.add(this.listener);
 
 		AnnotationAwareOrderComparator.sort(listeners);
 
-		assertThat(listeners).containsSequence(listener, otherListener);
+		assertThat(listeners).containsSequence(this.listener, otherListener);
+	}
+
+	@Test
+	// gh-3837
+	public void handlesGenericAnnotation() throws Exception {
+		Method method = ReflectionUtils.findMethod(
+				WithSecurityContextTestExecutionListenerTests.class,
+				"handlesGenericAnnotationTestMethod");
+		TestContext testContext = mock(TestContext.class);
+		when(testContext.getTestMethod()).thenReturn(method);
+		when(testContext.getApplicationContext())
+				.thenThrow(new IllegalStateException(""));
+
+		this.listener.beforeTestMethod(testContext);
+
+		assertThat(SecurityContextHolder.getContext().getAuthentication().getPrincipal())
+				.isInstanceOf(WithSuperClassWithSecurityContext.class);
+	}
+
+	@WithSuperClassWithSecurityContext
+	public void handlesGenericAnnotationTestMethod() {
+	}
+
+	@Retention(RetentionPolicy.RUNTIME)
+	@WithSecurityContext(factory = SuperClassWithSecurityContextFactory.class)
+	@interface WithSuperClassWithSecurityContext {
+		String username() default "WithSuperClassWithSecurityContext";
+	}
+
+	static class SuperClassWithSecurityContextFactory
+			implements WithSecurityContextFactory<Annotation> {
+
+		@Override
+		public SecurityContext createSecurityContext(Annotation annotation) {
+			SecurityContext context = SecurityContextHolder.createEmptyContext();
+			context.setAuthentication(new TestingAuthenticationToken(annotation, "NA"));
+			return context;
+		}
 	}
 }