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 e184e6a28d..f4a31feec3 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
@@ -31,7 +31,6 @@ import org.springframework.security.test.web.servlet.request.SecurityMockMvcRequ
 import org.springframework.test.context.TestContext;
 import org.springframework.test.context.TestExecutionListener;
 import org.springframework.test.context.support.AbstractTestExecutionListener;
-import org.springframework.test.util.MetaAnnotationUtils;
 import org.springframework.test.web.servlet.MockMvc;
 
 /**
@@ -61,10 +60,7 @@ public class WithSecurityContextTestExecutionListener extends AbstractTestExecut
 	 */
 	@Override
 	public void beforeTestMethod(TestContext testContext) {
-		TestSecurityContext testSecurityContext = createTestSecurityContext(testContext.getTestMethod(), testContext);
-		if (testSecurityContext == null) {
-			testSecurityContext = createTestSecurityContext(testContext.getTestClass(), testContext);
-		}
+		TestSecurityContext testSecurityContext = findTestSecurityContext(testContext);
 		if (testSecurityContext == null) {
 			return;
 		}
@@ -77,6 +73,21 @@ public class WithSecurityContextTestExecutionListener extends AbstractTestExecut
 		}
 	}
 
+	private TestSecurityContext findTestSecurityContext(TestContext testContext) {
+		TestSecurityContext testSecurityContext = createTestSecurityContext(testContext.getTestMethod(), testContext);
+		if (testSecurityContext != null) {
+			return testSecurityContext;
+		}
+		for (Class<?> classToSearch = testContext.getTestClass(); classToSearch != null; classToSearch = classToSearch
+				.getEnclosingClass()) {
+			testSecurityContext = createTestSecurityContext(classToSearch, testContext);
+			if (testSecurityContext != null) {
+				return testSecurityContext;
+			}
+		}
+		return null;
+	}
+
 	/**
 	 * If configured before test execution sets the SecurityContext
 	 * @since 5.1
@@ -97,10 +108,7 @@ public class WithSecurityContextTestExecutionListener extends AbstractTestExecut
 	}
 
 	private TestSecurityContext createTestSecurityContext(Class<?> annotated, TestContext context) {
-		MetaAnnotationUtils.AnnotationDescriptor<WithSecurityContext> withSecurityContextDescriptor = MetaAnnotationUtils
-				.findAnnotationDescriptor(annotated, WithSecurityContext.class);
-		WithSecurityContext withSecurityContext = (withSecurityContextDescriptor != null)
-				? withSecurityContextDescriptor.getAnnotation() : null;
+		WithSecurityContext withSecurityContext = AnnotationUtils.findAnnotation(annotated, WithSecurityContext.class);
 		return createTestSecurityContext(annotated, withSecurityContext, context);
 	}
 
diff --git a/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExcecutionListenerTests.java b/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExcecutionListenerTests.java
index e4849015f3..e29303ffbe 100644
--- a/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExcecutionListenerTests.java
+++ b/test/src/test/java/org/springframework/security/test/context/support/WithSecurityContextTestExcecutionListenerTests.java
@@ -92,6 +92,30 @@ public class WithSecurityContextTestExcecutionListenerTests {
 		assertThat(TestSecurityContextHolder.getContext().getAuthentication().getName()).isEqualTo("user");
 	}
 
+	@Test
+	@SuppressWarnings({ "rawtypes", "unchecked" })
+	public void beforeTestMethodInnerClass() throws Exception {
+		Class testClass = OuterClass.InnerClass.class;
+		Method testNoAnnotation = ReflectionUtils.findMethod(testClass, "testNoAnnotation");
+		given(this.testContext.getTestClass()).willReturn(testClass);
+		given(this.testContext.getTestMethod()).willReturn(testNoAnnotation);
+		given(this.testContext.getApplicationContext()).willThrow(new IllegalStateException(""));
+		this.listener.beforeTestMethod(this.testContext);
+		assertThat(TestSecurityContextHolder.getContext().getAuthentication().getName()).isEqualTo("user");
+	}
+
+	@Test
+	@SuppressWarnings({ "rawtypes", "unchecked" })
+	public void beforeTestMethodInnerInnerClass() throws Exception {
+		Class testClass = OuterClass.InnerClass.InnerInnerClass.class;
+		Method testNoAnnotation = ReflectionUtils.findMethod(testClass, "testNoAnnotation");
+		given(this.testContext.getTestClass()).willReturn(testClass);
+		given(this.testContext.getTestMethod()).willReturn(testNoAnnotation);
+		given(this.testContext.getApplicationContext()).willThrow(new IllegalStateException(""));
+		this.listener.beforeTestMethod(this.testContext);
+		assertThat(TestSecurityContextHolder.getContext().getAuthentication().getName()).isEqualTo("user");
+	}
+
 	// gh-3962
 	@Test
 	public void withSecurityContextAfterSqlScripts() {
@@ -166,4 +190,23 @@ public class WithSecurityContextTestExcecutionListenerTests {
 
 	}
 
+	@WithMockUser
+	static class OuterClass {
+
+		static class InnerClass {
+
+			void testNoAnnotation() {
+			}
+
+			static class InnerInnerClass {
+
+				void testNoAnnotation() {
+				}
+
+			}
+
+		}
+
+	}
+
 }