FULL PRODUCT VERSION :
javac 1.8.0_60

java version "1.8.0_60"
Java(TM) SE Runtime Environment (build 1.8.0_60-b27)
Java HotSpot(TM) 64-Bit Server VM (build 25.60-b23, mixed mode)

ADDITIONAL OS VERSION INFORMATION :
Likely platform independent...

4.2.0-16-generic #19-Ubuntu SMP Thu Oct 8 15:35:06 UTC 2015 x86_64 x86_64 x86_64 GNU/Linux

Ubuntu 12.04.5 LTS - 3.13.0-29-generic

Windows 7

A DESCRIPTION OF THE PROBLEM :
Type annotations placed on type parameters of supertypes are not accessible via reflection. I'm not sure why this is.

For example, consider the AnnotatedType produced by the following statement:

new @TestAnnotation ArrayList<@TestAnnotation List<Number>>() {}.getClass().getAnnotatedSuperclass()

the first annotation will be retained and reflected at runtime, but the second will be unavailable. This only happens with anonymous types.

STEPS TO FOLLOW TO REPRODUCE THE PROBLEM :
Simply run the simple test case provided. There are no external dependencies.

EXPECTED VERSUS ACTUAL BEHAVIOR :
EXPECTED -
Both annotations on:

new @TestAnnotation ArrayList<@TestAnnotation List<Number>>() {}.getClass().getAnnotatedSuperclass()

should be retained at runtime. The output of the source given below should be:

[@uk.co.strangeskies.reflection.test.FailTest$TestAnnotation()]
[@uk.co.strangeskies.reflection.test.FailTest$TestAnnotation()]
[@uk.co.strangeskies.reflection.test.FailTest$TestAnnotation()]
[@uk.co.strangeskies.reflection.test.FailTest$TestAnnotation()]
ACTUAL -
Only the first annotation on:

new @TestAnnotation ArrayList<@TestAnnotation List<Number>>() {}.getClass().getAnnotatedSuperclass()

is retained at runtime. The output of the source given below is:

[@uk.co.strangeskies.reflection.test.FailTest$TestAnnotation()]
[@uk.co.strangeskies.reflection.test.FailTest$TestAnnotation()]
[@uk.co.strangeskies.reflection.test.FailTest$TestAnnotation()]
[]

REPRODUCIBILITY :
This bug can be reproduced always.

---------- BEGIN SOURCE ----------
import java.lang.annotation.ElementType;
import java.lang.annotation.Retention;
import java.lang.annotation.RetentionPolicy;
import java.lang.annotation.Target;
import java.lang.reflect.AnnotatedParameterizedType;
import java.lang.reflect.AnnotatedType;
import java.util.ArrayList;
import java.util.Arrays;
import java.util.List;

@SuppressWarnings({ "javadoc", "serial" })
public class FailTest {
@Target(ElementType.TYPE_USE)
@Retention(RetentionPolicy.RUNTIME)
public @interface TestAnnotation {}

public class TestClass
extends @TestAnnotation ArrayList<@TestAnnotation List<Number>> {}

public void failTest() {
printAnnotations(TestClass.class.getAnnotatedSuperclass());

printAnnotations(
new @TestAnnotation ArrayList<@TestAnnotation List<Number>>() {}
.getClass().getAnnotatedSuperclass());

}

public void printAnnotations(AnnotatedType type) {
System.out.println(
Arrays.asList(((AnnotatedParameterizedType) type).getAnnotations()));

System.out.println(Arrays.asList(
((AnnotatedParameterizedType) type).getAnnotatedActualTypeArguments()[0]
.getAnnotations()));
}
}
---------- END SOURCE ----------

CUSTOMER SUBMITTED WORKAROUND :
None known.