diff --git a/common/values/optional_value.cc b/common/values/optional_value.cc
index 688cf8fb0..7c214b9cb 100644
--- a/common/values/optional_value.cc
+++ b/common/values/optional_value.cc
@@ -345,7 +345,7 @@ OpaqueValue GenericOptionalValueClone(
   cel::Value* absl_nonnull result =
       ::new (arena->AllocateAligned(sizeof(cel::Value), alignof(cel::Value)))
           cel::Value(content.To<OptionalValueContent>().value->Clone(arena));
-  if (!ArenaTraits<>::trivially_destructible(result)) {
+  if (!ArenaTraits<>::trivially_destructible(*result)) {
     arena->OwnDestructor(result);
   }
   return common_internal::MakeOptionalValue(
@@ -395,7 +395,7 @@ OptionalValue OptionalValue::Of(cel::Value value,
       cel::Value* absl_nonnull result = ::new (
           arena->AllocateAligned(sizeof(cel::Value), alignof(cel::Value)))
           cel::Value(std::move(value));
-      if (!ArenaTraits<>::trivially_destructible(result)) {
+      if (!ArenaTraits<>::trivially_destructible(*result)) {
         arena->OwnDestructor(result);
       }
       return OptionalValue(&optional_value_dispatcher,
diff --git a/runtime/BUILD b/runtime/BUILD
index 776a8223d..34ff411a1 100644
--- a/runtime/BUILD
+++ b/runtime/BUILD
@@ -615,6 +615,7 @@ cc_test(
         ":activation",
         ":constant_folding",
         ":function_adapter",
+        ":optional_types",
         ":reference_resolver",
         ":regex_precompilation",
         ":runtime",
diff --git a/runtime/memory_safety_test.cc b/runtime/memory_safety_test.cc
index 2a09be666..a60b4ce60 100644
--- a/runtime/memory_safety_test.cc
+++ b/runtime/memory_safety_test.cc
@@ -45,6 +45,7 @@
 #include "runtime/activation.h"
 #include "runtime/constant_folding.h"
 #include "runtime/function_adapter.h"
+#include "runtime/optional_types.h"
 #include "runtime/reference_resolver.h"
 #include "runtime/regex_precompilation.h"
 #include "runtime/runtime.h"
@@ -174,6 +175,7 @@ absl::StatusOr<std::unique_ptr<Runtime>> ConfigureRuntimeImpl(
   if (resolve_references) {
     CEL_RETURN_IF_ERROR(EnableReferenceResolver(
         runtime_builder, ReferenceResolverEnabled::kAlways));
+    CEL_RETURN_IF_ERROR(extensions::EnableOptionalTypes(runtime_builder));
   }
   if (evaluation_options == Options::kFoldConstants) {
     CEL_RETURN_IF_ERROR(extensions::EnableConstantFolding(runtime_builder));
@@ -315,6 +317,14 @@ INSTANTIATE_TEST_SUITE_P(
                 {{"condition", BoolValue(false)}},
                 test::StringValueIs("long_right_hand_string_0123456789"),
             },
+            {"optional_of_long_const_string",
+             "condition ? optional.of('lhs_short') : "
+             "optional.of('long_right_hand_string_0123456789')",
+             {{"condition", BoolValue(false)}},
+             test::OptionalValueIs(
+                 test::StringValueIs("long_right_hand_string_0123456789")),
+             // optional.of is a namespaced function.
+             /*enable_reference_resolver=*/true},
             {
                 "computed_string",
                 "(condition ? 'a.b' : 'b.c') + '.d.e.f'",