diff --git a/.changeset/fix-cli-kebab-flag-order.md b/.changeset/fix-cli-kebab-flag-order.md
new file mode 100644
index 000000000..d5db53521
--- /dev/null
+++ b/.changeset/fix-cli-kebab-flag-order.md
@@ -0,0 +1,5 @@
+---
+"openapi-typescript": patch
+---
+
+Fix CLI hanging when multi-word flags appear before the schema file argument. Flags such as `--enum-values`, `--path-params-as-types`, `--dedupe-enums`, `--empty-objects-unknown`, and others were not recognized as boolean by the argument parser when written in kebab-case, causing the schema path to be silently consumed as the flag's value and leaving the CLI waiting on stdin. Both camelCase and kebab-case forms are now registered as boolean.
diff --git a/packages/openapi-typescript/bin/cli.js b/packages/openapi-typescript/bin/cli.js
index 31be6e795..65834ce00 100755
--- a/packages/openapi-typescript/bin/cli.js
+++ b/packages/openapi-typescript/bin/cli.js
@@ -98,8 +98,14 @@ const BOOLEAN_FLAGS = [
   "rootTypesNoSchemaPrefix",
 ];
 
+// yargs-parser only recognizes boolean flags by their exact registered name,
+// so --enum-values (kebab-case) is not treated as boolean unless "enum-values"
+// is also in the boolean list. Generate kebab-case equivalents so positional
+// args after multi-word flags aren't silently consumed as flag values.
+const BOOLEAN_FLAGS_KEBAB = BOOLEAN_FLAGS.map((f) => f.replace(/([A-Z])/g, (c) => `-${c.toLowerCase()}`));
+
 const flags = parser(args, {
-  boolean: BOOLEAN_FLAGS,
+  boolean: [...BOOLEAN_FLAGS, ...BOOLEAN_FLAGS_KEBAB],
   string: ["output", "redocly"],
   alias: {
     redocly: ["c"],