diff --git a/test/auto_apply_version_metadata.py b/test/auto_apply_version_metadata.py
index 317c3bc..5dd8b5b 100644
--- a/test/auto_apply_version_metadata.py
+++ b/test/auto_apply_version_metadata.py
@@ -6,6 +6,10 @@ import re
 import datetime
 
 
+def get_comparable_version_tuple_from_string(version_string):
+    return tuple(map(int, version_string.split(".")))
+
+
 class PluginVersionMetadata:
     def __init__(self, plugin_name, version_name, plugin_path, from_json={}):
         self.plugin_name = plugin_name
@@ -69,6 +73,20 @@ class PluginVersionMetadata:
         md5sum = hashlib.md5(self._content).hexdigest()
         return md5sum
 
+    def sort_versions(self):
+        if self._content is None:
+            with open(self.plugin_path, "rb") as fin:
+                self._content = fin.read()
+
+        versions = self.json["plugins"][self.plugin_name]["versions"]
+        sorted_versions = dict(sorted(
+            tuple(versions.items()),
+            key=lambda version: get_comparable_version_tuple_from_string(version[0]),
+            reverse=True,
+        ))
+        self.json["plugins"][self.plugin_name]["versions"] = sorted_versions
+        return self
+
 
 class CategoryVersionMetadata:
     def __init__(self, category_metadata_base):
@@ -79,15 +97,14 @@ class CategoryVersionMetadata:
 
     def get_plugins_having_null_version_values(self):
         for plugin_name, plugin_metadata in self.category_metadata["plugins"].items():
-            latest_version_name, latest_version_metadata = tuple(
-                plugin_metadata["versions"].items())[0]
-            if latest_version_metadata is None:
-                plugin_path = f"{os.path.join(self.category_metadata_base, f'{plugin_name}.py')}"
-                yield PluginVersionMetadata(
-                    plugin_name,
-                    latest_version_name,
-                    plugin_path,
-                )
+            for version_name, version_metadata in plugin_metadata["versions"].items():
+                if version_metadata is None:
+                    plugin_path = f"{os.path.join(self.category_metadata_base, f'{plugin_name}.py')}"
+                    yield PluginVersionMetadata(
+                        plugin_name,
+                        version_name,
+                        plugin_path,
+                    )
 
     def get_plugins_having_diff_last_md5sum_version_values(self):
         for plugin_name, plugin_metadata in self.category_metadata["plugins"].items():
@@ -121,6 +138,7 @@ class CategoryVersionMetadata:
                       .set_commit_sha(commit_sha)
                       .set_released_on(today)
                       .set_md5sum()
+                      .sort_versions()
                       .json
             )
         return category_json