diff --git a/changelogs/fragments/fix_options.yml b/changelogs/fragments/fix_options.yml
new file mode 100644
index 00000000000..bf415ffc7f1
--- /dev/null
+++ b/changelogs/fragments/fix_options.yml
@@ -0,0 +1,2 @@
+bugfixes:
+    - allow set_options to be called multiple times https://github.com/ansible/ansible/pull/41913
diff --git a/lib/ansible/plugins/__init__.py b/lib/ansible/plugins/__init__.py
index dc629effb7e..92e99c39e4a 100644
--- a/lib/ansible/plugins/__init__.py
+++ b/lib/ansible/plugins/__init__.py
@@ -70,11 +70,10 @@ class AnsiblePlugin(with_metaclass(ABCMeta, object)):
         :arg var_options: Dict with either 'conneciton variables'
         :arg direct: Dict with 'direct assignment'
         '''
+        self._options = C.config.get_plugin_options(get_plugin_class(self), self._load_name, keys=task_keys, variables=var_options, direct=direct)
 
-        if not self._options:
-            # load config options if we have not done so already, if vars provided we should be mostly done
-            self._options = C.config.get_plugin_options(get_plugin_class(self), self._load_name, keys=task_keys, variables=var_options, direct=direct)
         # allow extras/wildcards from vars that are not directly consumed in configuration
+        # this is needed to support things like winrm that can have extended protocol options we don't direclty handle
         if self.allow_extras and var_options and '_extras' in var_options:
             self.set_option('_extras', var_options['_extras'])