diff --git a/src/test/java/org/openrewrite/staticanalysis/NullableOnMethodReturnTypeTest.java b/src/test/java/org/openrewrite/staticanalysis/NullableOnMethodReturnTypeTest.java
index 5eba00501..d87eab43a 100644
--- a/src/test/java/org/openrewrite/staticanalysis/NullableOnMethodReturnTypeTest.java
+++ b/src/test/java/org/openrewrite/staticanalysis/NullableOnMethodReturnTypeTest.java
@@ -16,6 +16,7 @@
 package org.openrewrite.staticanalysis;
 
 import org.junit.jupiter.api.Test;
+import org.junitpioneer.jupiter.ExpectedToFail;
 import org.openrewrite.DocumentExample;
 import org.openrewrite.test.RecipeSpec;
 import org.openrewrite.test.RewriteTest;
@@ -96,6 +97,39 @@ public class Foo {
         );
     }
 
+    @ExpectedToFail("Annotation is placed before the qualified name, producing `@Nullable Map.Entry` which javac rejects")
+    @Test
+    void moveNullableToNestedTypeSimpleName() {
+        rewriteRun(
+          //language=java
+          java(
+            """
+              import org.jspecify.annotations.Nullable;
+
+              import java.util.Map;
+
+              class Test<K, V> {
+                  @Nullable
+                  public Map.Entry<K, V> entry() {
+                      return null;
+                  }
+              }
+              """,
+            """
+              import org.jspecify.annotations.Nullable;
+
+              import java.util.Map;
+
+              class Test<K, V> {
+                  public Map.@Nullable Entry<K, V> entry() {
+                      return null;
+                  }
+              }
+              """
+          )
+        );
+    }
+
     @Test
     void dontTouchArguments() {
         rewriteRun(