diff --git a/include/CLI/Option.hpp b/include/CLI/Option.hpp
index f53986ec..e3403d8c 100644
--- a/include/CLI/Option.hpp
+++ b/include/CLI/Option.hpp
@@ -1075,6 +1075,7 @@ class Option : public OptionBase<Option> {
         add_result(val);
         run_callback();
         results_ = std::move(old_results);
+        current_option_state_ = option_state::parsing;
         return this;
     }
 
diff --git a/tests/TransformTest.cpp b/tests/TransformTest.cpp
index 25fd9fea..a3058e75 100644
--- a/tests/TransformTest.cpp
+++ b/tests/TransformTest.cpp
@@ -120,6 +120,25 @@ TEST_F(TApp, EnumCheckedDefualtTransform) {
     EXPECT_EQ(app.get_option("--existing")->as<existing>(), existing::abort);
 }
 
+// test from https://github.com/CLIUtils/CLI11/issues/369  [Jakub Zakrzewski](https://github.com/jzakrzewski)
+TEST_F(TApp, EnumCheckedDefaultTransformCallback) {
+    enum class existing : int16_t { abort, overwrite, remove };
+    auto cmd = std::make_shared<CLI::App>("deploys the repository somewhere", "deploy");
+    cmd->add_option("--existing", "What to do if file already exists in the destination")
+        ->transform(
+            CLI::CheckedTransformer(std::unordered_map<std::string, existing>{{"abort", existing::abort},
+                                                                              {"overwrite", existing::overwrite},
+                                                                              {"delete", existing::remove},
+                                                                              {"remove", existing::remove}}))
+        ->default_val("abort");
+
+    cmd->callback([cmd]() { EXPECT_EQ(cmd->get_option("--existing")->as<existing>(), existing::abort); });
+    app.add_subcommand(cmd);
+
+    args = {"deploy"};
+    run();
+}
+
 TEST_F(TApp, SimpleTransformFn) {
     int value;
     auto opt = app.add_option("-s", value)->transform(CLI::Transformer({{"one", "1"}}, CLI::ignore_case));