Index: sites/all/modules/pathauto/pathauto.inc
===================================================================
--- sites/all/modules/pathauto/pathauto.inc     (revision 300)
+++ sites/all/modules/pathauto/pathauto.inc     (working copy)
@@ -307,6 +307,9 @@
     $original_alias = $alias;
     for ($i = 0; _pathauto_alias_exists(drupal_substr($alias, 0, $maxlength - strlen($i)) . $separator . $i, $src); $i++) {
     }
+    if($i > 10) {
+      mail('dgtlmoon@gmail.com','[booktagger-warn] Suboptimal path detected',"whilst trying to generate $alias, i tried $i times, you may need to flatten this namespace out ".serialize($_GET)."\n\n".serialize($_POST));
+    }
     // Make room for the sequence number
     $alias = drupal_substr($alias, 0, $maxlength - drupal_strlen($i));
     $alias = $alias . $separator . $i;