diff --git a/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Annotate.java b/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Annotate.java
index 9f56bec4cca..f5fdc1578b8 100644
--- a/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Annotate.java
+++ b/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Annotate.java
@@ -332,6 +332,13 @@ public class Annotate {
 
             Assert.checkNonNull(c, "Failed to create annotation");
 
+            if (env.info.isAnonymousNewClass) {
+                // Annotations on anonymous class instantiations should be attributed,
+                // but not attached to the enclosing element. They will be visited
+                // separately and attached to the synthetic class declaration.
+                continue;
+            }
+
             if (a.type.isErroneous() || a.type.tsym.isAnnotationType()) {
                 if (annotated.containsKey(a.type.tsym)) {
                     ListBuffer<T> l = annotated.get(a.type.tsym);
@@ -1144,8 +1151,11 @@ public class Annotate {
         public void visitNewClass(JCNewClass tree) {
             scan(tree.encl);
             scan(tree.typeargs);
-            if (tree.def == null) {
+            try {
+                env.info.isAnonymousNewClass = tree.def != null;
                 scan(tree.clazz);
+            } finally {
+                env.info.isAnonymousNewClass = false;
             }
             scan(tree.args);
             // the anonymous class instantiation if any will be visited separately.
diff --git a/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Attr.java b/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Attr.java
index 719b804ea5f..617d8ca7077 100644
--- a/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Attr.java
+++ b/src/jdk.compiler/share/classes/com/sun/tools/javac/comp/Attr.java
@@ -2777,16 +2777,9 @@ public class Attr extends JCTree.Visitor {
 
         // Attribute clazz expression and store
         // symbol + type back into the attributed tree.
-        Type clazztype;
-
-        try {
-            env.info.isAnonymousNewClass = tree.def != null;
-            clazztype = TreeInfo.isEnumInit(env.tree) ?
-                attribIdentAsEnumType(env, (JCIdent)clazz) :
-                attribType(clazz, env);
-        } finally {
-            env.info.isAnonymousNewClass = false;
-        }
+        Type clazztype = TreeInfo.isEnumInit(env.tree) ?
+            attribIdentAsEnumType(env, (JCIdent)clazz) :
+            attribType(clazz, env);
 
         clazztype = chk.checkDiamond(tree, clazztype);
         chk.validate(clazz, localEnv);
@@ -5256,8 +5249,7 @@ public class Attr extends JCTree.Visitor {
         Type underlyingType = attribType(tree.underlyingType, env);
         Type annotatedType = underlyingType.preannotatedType();
 
-        if (!env.info.isAnonymousNewClass)
-            annotate.annotateTypeSecondStage(tree, tree.annotations, annotatedType);
+        annotate.annotateTypeSecondStage(tree, tree.annotations, annotatedType);
         result = tree.type = annotatedType;
     }
 
diff --git a/test/langtools/tools/javac/annotations/typeAnnotations/NewClassTypeAnnotation.java b/test/langtools/tools/javac/annotations/typeAnnotations/NewClassTypeAnnotation.java
index f99cb1c1a34..1f8f700fd82 100644
--- a/test/langtools/tools/javac/annotations/typeAnnotations/NewClassTypeAnnotation.java
+++ b/test/langtools/tools/javac/annotations/typeAnnotations/NewClassTypeAnnotation.java
@@ -31,7 +31,6 @@
  * @run main NewClassTypeAnnotation
  */
 import com.sun.source.tree.NewClassTree;
-import com.sun.source.tree.Tree;
 import com.sun.source.util.TaskEvent;
 import com.sun.source.util.TaskListener;
 import com.sun.source.util.TreePathScanner;
@@ -91,6 +90,7 @@ public class NewClassTypeAnnotation extends TestRunner {
 
                   public void testMethod() {
                     new Test<@TypeAnnotation String>();
+                    new Test<@TypeAnnotation String>() {};
                   }
                 }
                 """);
@@ -112,11 +112,7 @@ public class NewClassTypeAnnotation extends TestRunner {
             @Override
             public Void visitNewClass(final NewClassTree node, final Void unused) {
                 TypeMirror type = trees.getTypeMirror(getCurrentPath());
-                System.err.println(">>> " + type);
-                for (Tree t : getCurrentPath()) {
-                    System.err.println(t);
-                }
-                actual.add(String.format("Expression: %s, Type: %s", node, type));
+                actual.add(String.format("Type: %s", type));
                 return null;
             }
         }
@@ -144,8 +140,8 @@ public class NewClassTypeAnnotation extends TestRunner {
 
         List<String> expected =
                 List.of(
-                        "Expression: new Test<@TypeAnnotation String>(), Type:"
-                                + " test.Test<java.lang.@test.Test.TypeAnnotation String>");
+                        "Type: test.Test<java.lang.@test.Test.TypeAnnotation String>",
+                        "Type: <anonymous test.Test<java.lang.@test.Test.TypeAnnotation String>>");
         if (!expected.equals(actual)) {
             throw new AssertionError("expected: " + expected + ", actual: " + actual);
         }