diff --git a/java/src/com/github/bazel_contrib/contrib_rules_jvm/junit5/ActualRunner.java b/java/src/com/github/bazel_contrib/contrib_rules_jvm/junit5/ActualRunner.java
index f32dc277..3deea331 100644
--- a/java/src/com/github/bazel_contrib/contrib_rules_jvm/junit5/ActualRunner.java
+++ b/java/src/com/github/bazel_contrib/contrib_rules_jvm/junit5/ActualRunner.java
@@ -10,12 +10,16 @@
 import java.io.IOException;
 import java.io.PrintWriter;
 import java.io.UncheckedIOException;
+import java.lang.annotation.Annotation;
+import java.lang.reflect.InvocationTargetException;
+import java.lang.reflect.Modifier;
 import java.nio.file.Files;
 import java.nio.file.Path;
 import java.nio.file.Paths;
+import java.util.ArrayList;
 import java.util.Arrays;
-import java.util.Collections;
 import java.util.List;
+import java.util.stream.Collectors;
 import org.junit.platform.engine.DiscoverySelector;
 import org.junit.platform.engine.discovery.DiscoverySelectors;
 import org.junit.platform.launcher.Launcher;
@@ -47,11 +51,28 @@ public boolean run(String testClassName) {
               .addPostDiscoveryFilters(TestSharding.makeShardFilter())
               .build();
 
-      DiscoverySelector classSelector = DiscoverySelectors.selectClass(testClassName);
+      final Class<?> testClass;
+      try {
+        testClass = Class.forName(testClassName);
+      } catch (ClassNotFoundException e) {
+        throw new RuntimeException("Failed to find testClass", e);
+      }
+
+      // We only allow for one level of nesting at the moment
+      boolean enclosed = isRunWithEnclosed(testClass);
+      List<DiscoverySelector> classSelectors =
+          enclosed
+              ? new ArrayList<>()
+              : Arrays.stream(testClass.getDeclaredClasses())
+                  .filter(clazz -> Modifier.isStatic(clazz.getModifiers()))
+                  .map(clazz -> DiscoverySelectors.selectClass(clazz))
+                  .collect(Collectors.toList());
+
+      classSelectors.add(DiscoverySelectors.selectClass(testClassName));
 
       LauncherDiscoveryRequestBuilder request =
           LauncherDiscoveryRequestBuilder.request()
-              .selectors(Collections.singletonList(classSelector))
+              .selectors(classSelectors)
               .configurationParameter(LauncherConstants.CAPTURE_STDERR_PROPERTY_NAME, "true")
               .configurationParameter(LauncherConstants.CAPTURE_STDOUT_PROPERTY_NAME, "true");
 
@@ -98,6 +119,27 @@ public boolean run(String testClassName) {
     }
   }
 
+  /**
+   * Checks if the test class is annotation with `@RunWith(Enclosed.class)`. We deliberately avoid
+   * using types here to avoid polluting the classpath with junit4 deps.
+   */
+  private boolean isRunWithEnclosed(Class<?> clazz) {
+    for (Annotation annotation : clazz.getAnnotations()) {
+      Class<? extends Annotation> type = annotation.annotationType();
+      if (type.getName().equals("org.junit.runner.RunWith")) {
+        try {
+          Class<?> runner = (Class<?>) type.getMethod("value").invoke(annotation, (Object[]) null);
+          if (runner.getName().equals("org.junit.experimental.runners.Enclosed")) {
+            return true;
+          }
+        } catch (NoSuchMethodException | IllegalAccessException | InvocationTargetException e) {
+          return false;
+        }
+      }
+    }
+    return false;
+  }
+
   private File getExitFile() {
     String exitFileName = System.getenv("TEST_PREMATURE_EXIT_FILE");
     if (exitFileName == null) {
diff --git a/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/BUILD.bazel b/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/BUILD.bazel
index 1b5cd67f..68e5a924 100644
--- a/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/BUILD.bazel
+++ b/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/BUILD.bazel
@@ -16,12 +16,16 @@ SHARDING_TEST = [
     "ShardingTest.java",
 ]
 
+VINTAGE_NESTED_TEST = [
+    "NestedClassesVintageTest.java",
+]
+
 java_test_suite(
     name = "small-tests",
     size = "small",
     srcs = glob(
         ["*.java"],
-        exclude = PACKAGE_NAME_TEST + PARALLEL_TEST + SHARDING_TEST,
+        exclude = PACKAGE_NAME_TEST + PARALLEL_TEST + SHARDING_TEST + VINTAGE_NESTED_TEST,
     ),
     exclude_engines = ["junit-vintage"],
     include_engines = ["junit-jupiter"],
@@ -36,6 +40,20 @@ java_test_suite(
     ] + junit5_vintage_deps("contrib_rules_jvm_tests"),
 )
 
+java_test_suite(
+    name = "vintage-nested-test",
+    size = "small",
+    srcs = [
+        "NestedClassesVintageTest.java",
+    ],
+    exclude_engines = ["junit-jupiter"],
+    include_engines = ["junit-vintage"],
+    runner = "junit5",
+    deps = [
+        "//java/src/com/github/bazel_contrib/contrib_rules_jvm/junit5",
+    ] + junit5_vintage_deps("contrib_rules_jvm_tests"),
+)
+
 # Test that we can set the package name properly. We do this by
 # setting the `package` attribute deliberately rather than letting
 # the value be guessed at by the runner.
diff --git a/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/NestedClassesTest.java b/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/NestedClassesTest.java
new file mode 100644
index 00000000..d0364e4e
--- /dev/null
+++ b/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/NestedClassesTest.java
@@ -0,0 +1,28 @@
+package com.github.bazel_contrib.contrib_rules_jvm.junit5;
+
+import edu.umd.cs.findbugs.annotations.SuppressFBWarnings;
+import org.junit.jupiter.api.Nested;
+import org.junit.jupiter.api.Test;
+
+public class NestedClassesTest {
+  static class First {
+    @Test
+    public void shouldBeExecuted() {
+      System.out.println(">>>> Executed test in NestedClassesTest$First");
+    }
+  }
+
+  @Nested
+  @SuppressFBWarnings("SIC_INNER_SHOULD_BE_STATIC")
+  class Second {
+    @Test
+    public void shouldBeExecuted() {
+      System.out.println(">>>> Executed test in NestedClassesTest$Second");
+    }
+  }
+
+  @Test
+  public void shouldBeExecuted() {
+    System.out.println(">>>> Executed test in NestedClassesTest");
+  }
+}
diff --git a/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/NestedClassesVintageTest.java b/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/NestedClassesVintageTest.java
new file mode 100644
index 00000000..1507da00
--- /dev/null
+++ b/java/test/com/github/bazel_contrib/contrib_rules_jvm/junit5/NestedClassesVintageTest.java
@@ -0,0 +1,15 @@
+package com.github.bazel_contrib.contrib_rules_jvm.junit5;
+
+import org.junit.Test;
+import org.junit.experimental.runners.Enclosed;
+import org.junit.runner.RunWith;
+
+@RunWith(Enclosed.class)
+public class NestedClassesVintageTest {
+  public static class First {
+    @Test
+    public void shouldBeExecuted() {
+      System.out.println(">>>> Executed test in NestedClassesVintageTest$First");
+    }
+  }
+}