diff --git a/test/ruby/test_class.rb b/test/ruby/test_class.rb
index f40817e7a1..10b7655e9a 100644
--- a/test/ruby/test_class.rb
+++ b/test/ruby/test_class.rb
@@ -887,4 +887,34 @@ CODE
       class C; end
     end;
   end
+
+  def test_singleton_cc_invalidation
+    assert_separately([], "#{<<~"begin;"}\n#{<<~"end;"}")
+    begin;
+      class T
+        def hi
+          "hi"
+        end
+      end
+
+      t = T.new
+      t.singleton_class
+
+      def hello(t)
+        t.hi
+      end
+
+      5.times do
+        hello(t) # populate inline cache on `t.singleton_class`.
+      end
+
+      class T
+        remove_method :hi # invalidate `t.singleton_class` ccs for `hi`
+      end
+
+      assert_raise NoMethodError do
+        hello(t)
+      end
+    end;
+  end
 end