diff --git a/java/java-impl/src/com/intellij/codeInsight/ExternalAnnotationsManagerImpl.java b/java/java-impl/src/com/intellij/codeInsight/ExternalAnnotationsManagerImpl.java
index 72f442e407b4..991a7e1dea9e 100644
--- a/java/java-impl/src/com/intellij/codeInsight/ExternalAnnotationsManagerImpl.java
+++ b/java/java-impl/src/com/intellij/codeInsight/ExternalAnnotationsManagerImpl.java
@@ -16,12 +16,11 @@ import com.intellij.openapi.command.undo.BasicUndoableAction;
 import com.intellij.openapi.command.undo.UndoManager;
 import com.intellij.openapi.command.undo.UndoUtil;
 import com.intellij.openapi.diagnostic.Logger;
-import com.intellij.openapi.editor.Document;
-import com.intellij.openapi.editor.Editor;
-import com.intellij.openapi.editor.LogicalPosition;
-import com.intellij.openapi.editor.ScrollType;
+import com.intellij.openapi.editor.*;
 import com.intellij.openapi.editor.colors.EditorColors;
 import com.intellij.openapi.editor.colors.EditorColorsManager;
+import com.intellij.openapi.editor.event.DocumentEvent;
+import com.intellij.openapi.editor.event.DocumentListener;
 import com.intellij.openapi.editor.markup.RangeHighlighter;
 import com.intellij.openapi.editor.markup.TextAttributes;
 import com.intellij.openapi.fileChooser.FileChooser;
@@ -50,10 +49,7 @@ import com.intellij.psi.codeStyle.JavaCodeStyleSettings;
 import com.intellij.psi.xml.XmlDocument;
 import com.intellij.psi.xml.XmlFile;
 import com.intellij.psi.xml.XmlTag;
-import com.intellij.util.ArrayUtil;
-import com.intellij.util.IncorrectOperationException;
-import com.intellij.util.Processor;
-import com.intellij.util.SmartList;
+import com.intellij.util.*;
 import com.intellij.util.containers.ContainerUtil;
 import com.intellij.util.messages.MessageBus;
 import com.intellij.util.ui.OptionsMessageDialog;
@@ -77,8 +73,10 @@ import java.util.Set;
  */
 public class ExternalAnnotationsManagerImpl extends ReadableExternalAnnotationsManager {
   private static final Logger LOG = Logger.getInstance(ExternalAnnotationsManagerImpl.class);
+  public static final long ANNOTATION_EDITED_TIMEOUT_MILLIS = 100;
 
   private final MessageBus myBus;
+  private final Alarm myAnnotationDocumentEdited;
 
   public ExternalAnnotationsManagerImpl(@NotNull final Project project, final PsiManager psiManager) {
     super(psiManager);
@@ -91,6 +89,8 @@ public class ExternalAnnotationsManagerImpl extends ReadableExternalAnnotationsM
     });
 
     VirtualFileManager.getInstance().addVirtualFileListener(new MyVirtualFileListener(), project);
+    myAnnotationDocumentEdited = new Alarm(Alarm.ThreadToUse.SWING_THREAD, project);
+    EditorFactory.getInstance().getEventMulticaster().addDocumentListener(new MyDocumentListener(), project);
   }
 
   private void notifyAfterAnnotationChanging(@NotNull PsiModifierListOwner owner, @NotNull String annotationFQName, boolean successful) {
@@ -847,4 +847,18 @@ public class ExternalAnnotationsManagerImpl extends ReadableExternalAnnotationsM
       processEvent(event);
     }
   }
+
+  private class MyDocumentListener implements DocumentListener {
+
+    final FileDocumentManager myFileDocumentManager = FileDocumentManager.getInstance();
+
+    @Override
+    public void documentChanged(DocumentEvent event) {
+      final VirtualFile file = myFileDocumentManager.getFile(event.getDocument());
+      if (file != null && ANNOTATIONS_XML.equals(file.getName()) && isUnderAnnotationRoot(file)) {
+        myAnnotationDocumentEdited.cancelAllRequests();
+        myAnnotationDocumentEdited.addRequest(() -> dropCache(), ANNOTATION_EDITED_TIMEOUT_MILLIS);
+      }
+    }
+  }
 }
diff --git a/java/java-tests/testData/codeInsight/externalAnnotations/content/anno/edit/annotations.xml b/java/java-tests/testData/codeInsight/externalAnnotations/content/anno/edit/annotations.xml
new file mode 100644
index 000000000000..abd01e3a9064
--- /dev/null
+++ b/java/java-tests/testData/codeInsight/externalAnnotations/content/anno/edit/annotations.xml
@@ -0,0 +1,3 @@
+<root>
+  <item name='edit.Foo'><annotation name='java.lang.Deprecated'/></item><caret>
+</root>
\ No newline at end of file
diff --git a/java/java-tests/testData/codeInsight/externalAnnotations/lib/edit/Foo.java b/java/java-tests/testData/codeInsight/externalAnnotations/lib/edit/Foo.java
new file mode 100644
index 000000000000..65269e0ab137
--- /dev/null
+++ b/java/java-tests/testData/codeInsight/externalAnnotations/lib/edit/Foo.java
@@ -0,0 +1,2 @@
+package edit;
+public class Foo {}
\ No newline at end of file
diff --git a/java/java-tests/testSrc/com/intellij/java/codeInsight/AddAnnotationFixTest.java b/java/java-tests/testSrc/com/intellij/java/codeInsight/AddAnnotationFixTest.java
index d8d58f83b9cc..75ce07b3facc 100644
--- a/java/java-tests/testSrc/com/intellij/java/codeInsight/AddAnnotationFixTest.java
+++ b/java/java-tests/testSrc/com/intellij/java/codeInsight/AddAnnotationFixTest.java
@@ -5,6 +5,7 @@ import com.intellij.codeInsight.AnnotationUtil;
 import com.intellij.codeInsight.ExternalAnnotationsListener;
 import com.intellij.codeInsight.ExternalAnnotationsManager;
 import com.intellij.codeInsight.NullableNotNullManager;
+import com.intellij.codeInsight.generation.actions.CommentByLineCommentAction;
 import com.intellij.codeInsight.intention.AddAnnotationPsiFix;
 import com.intellij.codeInsight.intention.impl.AnnotateIntentionAction;
 import com.intellij.codeInsight.intention.impl.DeannotateIntentionAction;
@@ -36,6 +37,7 @@ import com.intellij.testFramework.builders.JavaModuleFixtureBuilder;
 import com.intellij.testFramework.fixtures.*;
 import com.intellij.util.ObjectUtils;
 import com.intellij.util.messages.MessageBusConnection;
+import com.intellij.util.ui.UIUtil;
 import org.jetbrains.annotations.NonNls;
 import org.jetbrains.annotations.NotNull;
 
@@ -44,6 +46,8 @@ import java.util.ArrayList;
 import java.util.Collections;
 import java.util.List;
 
+import static com.intellij.psi.impl.DebugUtil.sleep;
+
 /**
  * @author anna
  * @since 27-Jun-2007
@@ -368,6 +372,25 @@ public class AddAnnotationFixTest extends UsefulTestCase {
     stopListeningAndCheckEvents();
   }
 
+
+  public void testAnnotationsUpdatedWhenFileEdited() {
+    addDefaultLibrary();
+    final PsiFile[] files = myFixture.configureByFiles("/content/anno/edit/annotations.xml", "lib/edit/Foo.java");
+    final PsiClass fooJava = ((PsiClassOwner)files[1]).getClasses()[0];
+    ExternalAnnotationsManager.getInstance(myProject);
+
+    PsiAnnotation annotation = AnnotationUtil.findAnnotation(fooJava, "java.lang.Deprecated");
+    assertNotNull(annotation);
+    assertEquals("java.lang.Deprecated", annotation.getQualifiedName());
+
+    startListeningForExternalChanges();
+    myFixture.testAction(new CommentByLineCommentAction()); // comment out a line in annotations file
+    sleep(150);
+    UIUtil.dispatchAllInvocationEvents();
+    annotation = AnnotationUtil.findAnnotation(fooJava, "java.lang.Deprecated");
+    assertNull(annotation);
+  }
+
   private class DefaultAnnotationsListener extends ExternalAnnotationsListener.Adapter {
     @Override
     public void afterExternalAnnotationChanging(@NotNull PsiModifierListOwner owner, @NotNull String annotationFQName,