Token authentication- "The form has become outdated" and rules issues
From my point of view, it would seem Rules are not being triggered at all. You could, however, try invoking a rule manually by placing a rules_invoke_event() call within inside a custom form submit function.

Note that the #submit property on Drupal forms allow multiple submit handlers to be called for a single form.

In the hook_form_privatemsg_new_alter() and hook_form_privatemsg_form_reply_alter() form alters you have implemented you should be able to find and modify the #submit property. Just do something like:

// Implementation of hook_form_FORMID_alter().
patricks_form_privatemsg_new_alter($form, &amp;$form_state) {
  ...
  $form['#submit'][] = 'patricks_privatemsg_submit';
  return $form;
}


Then in your submit handler you can use the rules_invoke_event():

function patricks_privatemsg_submit($form, &amp;$form_state) {
   drupal_set_message(t('The form has been submitted.'));
   // Pass parameters for the variables provided by this event, as defined in hook_rules_event_info()...
   rules_invoke_event('privmsg_foo_rule', $foos, $barf, $bam);
}


If for some reason you get a rules_invoke_event() function not found error, just add a module_load_include() to your submit handler before invoking the rule.