diff --git a/src/main/java/com/android/tools/r8/shaking/AnnotationRemover.java b/src/main/java/com/android/tools/r8/shaking/AnnotationRemover.java
index 0c47df1..d194bb2 100644
--- a/src/main/java/com/android/tools/r8/shaking/AnnotationRemover.java
+++ b/src/main/java/com/android/tools/r8/shaking/AnnotationRemover.java
@@ -11,8 +11,10 @@
 import com.android.tools.r8.graph.DexItemFactory;
 import com.android.tools.r8.graph.DexProgramClass;
 import com.android.tools.r8.graph.DexType;
+import com.android.tools.r8.graph.InnerClassAttribute;
 import com.android.tools.r8.shaking.Enqueuer.AppInfoWithLiveness;
 import com.android.tools.r8.utils.InternalOptions;
+import java.util.List;
 
 public class AnnotationRemover {
 
@@ -135,11 +137,36 @@
     field.annotations = field.annotations.keepIf(this::filterAnnotations);
   }
 
+  private boolean enclosingMethodPinned(DexClass clazz) {
+    return clazz.getEnclosingMethod() != null
+        && clazz.getEnclosingMethod().getEnclosingClass() != null
+        && appInfo.isPinned(clazz.getEnclosingMethod().getEnclosingClass());
+  }
+
+  private boolean innerClassPinned(DexClass clazz) {
+    List<InnerClassAttribute> innerClasses = clazz.getInnerClasses();
+    for (InnerClassAttribute innerClass : innerClasses) {
+      if (appInfo.isPinned(innerClass.getInner())) {
+        return true;
+      }
+      if (appInfo.isPinned(innerClass.getOuter())) {
+        return true;
+      }
+    }
+    return false;
+  }
+
   private void stripAttributes(DexProgramClass clazz) {
     // If [clazz] is mentioned by a keep rule, it could be used for reflection, and we therefore
     // need to keep the enclosing method and inner classes attributes, if requested. In Proguard
     // compatibility mode we keep these attributes independent of whether the given class is kept.
-    if (appInfo.isPinned(clazz.type) || options.forceProguardCompatibility) {
+    // To ensure reflection from both inner to outer and and outer to inner for kept classes - even
+    // if only one side is kept - keep the attributes is any class mentioned in these attributes
+    // is kept.
+    if (appInfo.isPinned(clazz.type)
+        || enclosingMethodPinned(clazz)
+        || innerClassPinned(clazz)
+        || options.forceProguardCompatibility) {
       if (!keep.enclosingMethod) {
         clazz.clearEnclosingMethod();
       }
diff --git a/src/test/java/com/android/tools/r8/shaking/innerclassesenclosingmethod/KeepInnerClassesEnclosingMethodAnnotationsTest.java b/src/test/java/com/android/tools/r8/shaking/innerclassesenclosingmethod/KeepInnerClassesEnclosingMethodAnnotationsTest.java
new file mode 100644
index 0000000..474194e
--- /dev/null
+++ b/src/test/java/com/android/tools/r8/shaking/innerclassesenclosingmethod/KeepInnerClassesEnclosingMethodAnnotationsTest.java
@@ -0,0 +1,141 @@
+// Copyright (c) 2018, the R8 project authors. Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+package com.android.tools.r8.shaking.innerclassesenclosingmethod;
+
+import static com.android.tools.r8.utils.codeinspector.Matchers.isMemberClass;
+import static com.android.tools.r8.utils.codeinspector.Matchers.isPresent;
+import static com.android.tools.r8.utils.codeinspector.Matchers.isRenamed;
+import static org.hamcrest.CoreMatchers.not;
+import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertThat;
+
+import com.android.tools.r8.R8Command;
+import com.android.tools.r8.TestBase;
+import com.android.tools.r8.ToolHelper;
+import com.android.tools.r8.origin.Origin;
+import com.android.tools.r8.shaking.innerclassesenclosingmethod.testclasses.Outer;
+import com.android.tools.r8.utils.AndroidApp;
+import com.android.tools.r8.utils.StringUtils;
+import com.android.tools.r8.utils.codeinspector.ClassSubject;
+import com.android.tools.r8.utils.codeinspector.CodeInspector;
+import com.google.common.collect.ImmutableList;
+import java.util.List;
+import org.junit.Test;
+
+class Main {
+
+  public static void main(String[] args) {
+    Class<?>[] declaredClasses = Outer.class.getDeclaredClasses();
+    if (declaredClasses.length == 0) {
+      System.out.println("No declared classes");
+    } else {
+      for (int i = 0; i < declaredClasses.length; i++) {
+        System.out.println("Declared class: " + declaredClasses[i].getName());
+      }
+    }
+    if (Outer.Inner.class.getDeclaringClass() == null) {
+      System.out.println("No declaring classes");
+    } else {
+      System.out.println("Declaring class: " + Outer.Inner.class.getDeclaringClass().getName());
+    }
+  }
+}
+
+public class KeepInnerClassesEnclosingMethodAnnotationsTest extends TestBase {
+  private static class TestResult {
+
+    public final AndroidApp app;
+    public final CodeInspector inspector;
+    public final ClassSubject outer;
+    public final ClassSubject inner;
+
+    TestResult(AndroidApp app) throws Throwable {
+      this.app = app;
+      this.inspector = new CodeInspector(app);
+      this.outer = inspector.clazz(Outer.class);
+      this.inner = inspector.clazz(Outer.Inner.class);
+      assertThat(outer, isPresent());
+      assertThat(inner, isPresent());
+    }
+  }
+
+  private TestResult runTest(List<String> proguardConfiguration) throws Throwable {
+    return new TestResult(
+        ToolHelper.runR8(
+            R8Command.builder()
+                .addProgramFiles(ToolHelper.getClassFilesForTestPackage(Outer.class.getPackage()))
+                .addClassProgramData(ToolHelper.getClassAsBytes(Main.class), Origin.unknown())
+                .addProguardConfiguration(proguardConfiguration, Origin.unknown())
+                .setProgramConsumer(emptyConsumer(Backend.DEX))
+                .build()));
+  }
+
+  private void noInnerClassesEnclosingMethodInformation(TestResult result) throws Throwable {
+    List<String> lines = StringUtils.splitLines(runOnArt(result.app, Main.class));
+    assertEquals(2, lines.size());
+    assertEquals("No declared classes", lines.get(0));
+    assertEquals("No declaring classes", lines.get(1));
+  }
+
+  private void fullInnerClassesEnclosingMethodInformation(TestResult result) throws Throwable {
+    List<String> lines = StringUtils.splitLines(runOnArt(result.app, Main.class));
+    assertEquals(2, lines.size());
+    assertEquals("Declared class: " + result.inner.getFinalName(), lines.get(0));
+    assertEquals("Declaring class: " + result.outer.getFinalName(), lines.get(1));
+  }
+
+  @Test
+  public void testKeepAll() throws Throwable {
+    TestResult result =
+        runTest(
+            ImmutableList.of(
+                "-keepattributes InnerClasses,EnclosingMethod",
+                "-keep class **Outer*",
+                keepMainProguardConfiguration(Main.class)));
+    assertThat(result.outer, not(isRenamed()));
+    assertThat(result.inner, not(isRenamed()));
+    assertThat(result.inner, isMemberClass());
+    fullInnerClassesEnclosingMethodInformation(result);
+  }
+
+  @Test
+  public void testKeepAllWithoutAttributes() throws Throwable {
+    TestResult result =
+        runTest(
+            ImmutableList.of("-keep class **Outer*", keepMainProguardConfiguration(Main.class)));
+    assertThat(result.outer, not(isRenamed()));
+    assertThat(result.inner, not(isRenamed()));
+    assertThat(result.inner, not(isMemberClass()));
+    noInnerClassesEnclosingMethodInformation(result);
+  }
+
+  @Test
+  public void testKeepInner() throws Throwable {
+    TestResult result =
+        runTest(
+            ImmutableList.of(
+                "-keepattributes InnerClasses,EnclosingMethod",
+                "-keep class **Outer$Inner",
+                keepMainProguardConfiguration(Main.class)));
+    assertThat(result.outer, isRenamed());
+    assertThat(result.inner, not(isRenamed()));
+    assertThat(result.inner, isMemberClass());
+    fullInnerClassesEnclosingMethodInformation(result);
+  }
+
+  @Test
+  public void testKeepOuter() throws Throwable {
+    TestResult result =
+        runTest(
+            ImmutableList.of(
+                "-keepattributes InnerClasses,EnclosingMethod",
+                "-keep class **Outer",
+                keepMainProguardConfiguration(Main.class)));
+    assertThat(result.outer, not(isRenamed()));
+    assertThat(result.inner, isRenamed());
+    assertThat(result.inner, isMemberClass());
+    fullInnerClassesEnclosingMethodInformation(result);
+  }
+}
diff --git a/src/test/java/com/android/tools/r8/shaking/innerclassesenclosingmethod/testclasses/Outer.java b/src/test/java/com/android/tools/r8/shaking/innerclassesenclosingmethod/testclasses/Outer.java
new file mode 100644
index 0000000..064583f
--- /dev/null
+++ b/src/test/java/com/android/tools/r8/shaking/innerclassesenclosingmethod/testclasses/Outer.java
@@ -0,0 +1,10 @@
+// Copyright (c) 2018, the R8 project authors. Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+package com.android.tools.r8.shaking.innerclassesenclosingmethod.testclasses;
+
+public class Outer {
+
+  public static class Inner {}
+}
diff --git a/src/test/java/com/android/tools/r8/utils/codeinspector/Matchers.java b/src/test/java/com/android/tools/r8/utils/codeinspector/Matchers.java
index 3b718a4..7f310ed 100644
--- a/src/test/java/com/android/tools/r8/utils/codeinspector/Matchers.java
+++ b/src/test/java/com/android/tools/r8/utils/codeinspector/Matchers.java
@@ -115,6 +115,25 @@
     };
   }
 
+  public static Matcher<ClassSubject> isMemberClass() {
+    return new TypeSafeMatcher<ClassSubject>() {
+      @Override
+      public boolean matchesSafely(final ClassSubject clazz) {
+        return clazz.isMemberClass();
+      }
+
+      @Override
+      public void describeTo(final Description description) {
+        description.appendText("is member class");
+      }
+
+      @Override
+      public void describeMismatchSafely(final ClassSubject clazz, Description description) {
+        description.appendText("class ").appendValue(clazz.getOriginalName()).appendText(" is not");
+      }
+    };
+  }
+
   public static Matcher<MethodSubject> isAbstract() {
     return new TypeSafeMatcher<MethodSubject>() {
       @Override