diff --git a/include/chaiscript/dispatchkit/dynamic_object_detail.hpp b/include/chaiscript/dispatchkit/dynamic_object_detail.hpp
index 1a599d0a..e9c8012e 100644
--- a/include/chaiscript/dispatchkit/dynamic_object_detail.hpp
+++ b/include/chaiscript/dispatchkit/dynamic_object_detail.hpp
@@ -103,7 +103,9 @@ namespace chaiscript {
 
           assert(types.size() > 1);
           // assert(types[1].bare_equal(user_type<Boxed_Value>()));
-          types[1] = t_objectti;
+          // When the object type_info is undefined (ChaiScript-defined class), use
+          // Dynamic_Object so that dispatch priority scoring works correctly.
+          types[1] = t_objectti.is_undef() ? user_type<Dynamic_Object>() : t_objectti;
           return types;
         }
 
diff --git a/include/chaiscript/dispatchkit/proxy_functions.hpp b/include/chaiscript/dispatchkit/proxy_functions.hpp
index 002e473b..326fa257 100644
--- a/include/chaiscript/dispatchkit/proxy_functions.hpp
+++ b/include/chaiscript/dispatchkit/proxy_functions.hpp
@@ -380,7 +380,15 @@ namespace chaiscript {
 
         for (const auto &t : t_types.types()) {
           if (t.second.is_undef()) {
-            types.push_back(chaiscript::detail::Get_Type_Info<Boxed_Value>::get());
+            if (!t.first.empty()) {
+              // Named type without C++ type_info — assumed to be a Dynamic_Object subtype.
+              // Using Dynamic_Object type_info ensures correct dispatch priority so that
+              // user-defined overrides on specific subtypes are tried before generic
+              // Dynamic_Object built-in functions.
+              types.push_back(user_type<Dynamic_Object>());
+            } else {
+              types.push_back(chaiscript::detail::Get_Type_Info<Boxed_Value>::get());
+            }
           } else {
             types.push_back(t.second);
           }
@@ -806,6 +814,30 @@ namespace chaiscript {
             numdiffs = plist.size();
           }
 
+          // Deprioritize C++ registered generic Dynamic_Object functions when the
+          // actual first argument is a specific Dynamic_Object subtype.  This allows
+          // user-defined operator overrides (e.g. `[]`) on a subtype to take precedence
+          // over the built-in Dynamic_Object operations such as get_attr.
+          // Only deprioritize non-dynamic (C++ registered) functions — ChaiScript-defined
+          // functions (Dynamic_Proxy_Function) have their own type matching via Param_Types.
+          if (!plist.empty()
+              && dynamic_cast<const Dynamic_Proxy_Function *>(func.get()) == nullptr) {
+            static const auto dynamic_object_ti = user_type<Dynamic_Object>();
+            if (func->get_param_types().size() > 1
+                && func->get_param_types()[1].bare_equal(dynamic_object_ti)
+                && plist[0].get_type_info().bare_equal(dynamic_object_ti)
+                && func->dynamic_object_type_name().empty()) {
+              try {
+                const auto &d = boxed_cast<const Dynamic_Object &>(plist[0], &t_conversions);
+                if (d.get_type_name() != "Dynamic_Object") {
+                  numdiffs = plist.size();
+                }
+              } catch (const std::bad_cast &) {
+                // not a Dynamic_Object, ignore
+              }
+            }
+          }
+
           ordered_funcs.emplace_back(numdiffs, func.get());
         }
       }
diff --git a/unittests/index_operator_override.chai b/unittests/index_operator_override.chai
new file mode 100644
index 00000000..2a3d89c3
--- /dev/null
+++ b/unittests/index_operator_override.chai
@@ -0,0 +1,45 @@
+
+// Test overriding [] operator with various index types (issue #398)
+
+class my_class
+{
+  def my_class()
+  {
+  }
+};
+
+def `[]`(my_class o, idx)
+{
+  return "Hello World!";
+}
+
+var o = my_class();
+
+// Integer index should work
+assert_equal("Hello World!", o[3]);
+
+// String index should work
+assert_equal("Hello World!", o["3"]);
+
+// String variable as index should work
+var s = "abc";
+assert_equal("Hello World!", o[s]);
+
+// Typed string parameter override
+class my_class2
+{
+  def my_class2()
+  {
+  }
+};
+
+def `[]`(my_class2 o, string key)
+{
+  return "key=" + key;
+}
+
+var o2 = my_class2();
+assert_equal("key=foo", o2["foo"]);
+
+var key = "bar";
+assert_equal("key=bar", o2[key]);