diff --git a/evennia/contrib/rpsystem.py b/evennia/contrib/rpsystem.py
index 34a78db166..5d1957bea5 100644
--- a/evennia/contrib/rpsystem.py
+++ b/evennia/contrib/rpsystem.py
@@ -238,7 +238,7 @@ def ordered_permutation_regex(sentence):
             solution.append(_PREFIX + r"[0-9]*%s*%s(?=\W|$)+" % (_NUM_SEP, re_escape(" ".join(comb)).rstrip("\\")))
 
     # combine into a match regex, first matching the longest down to the shortest components
-    regex = r"|".join(sorted(set(solution), key=len, reverse=True))
+    regex = r"|".join(sorted(set(solution), key=lambda item: (-len(item), item)))
     return regex
 
 
diff --git a/evennia/contrib/tests.py b/evennia/contrib/tests.py
index 8a61078e85..c3db584318 100644
--- a/evennia/contrib/tests.py
+++ b/evennia/contrib/tests.py
@@ -107,12 +107,22 @@ class TestRPSystem(EvenniaTest):
     def test_ordered_permutation_regex(self):
         self.assertEqual(
             rpsystem.ordered_permutation_regex(sdesc0),
-            '/[0-9]*-*A\\ nice\\ sender\\ of\\ emotes(?=\\W|$)+|/[0-9]*-*nice\\ sender\\ '
-            'of\\ emotes(?=\\W|$)+|/[0-9]*-*A\\ nice\\ sender\\ of(?=\\W|$)+|/[0-9]*-*sender\\ '
-            'of\\ emotes(?=\\W|$)+|/[0-9]*-*nice\\ sender\\ of(?=\\W|$)+|/[0-9]*-*A\\ nice\\ '
-            'sender(?=\\W|$)+|/[0-9]*-*nice\\ sender(?=\\W|$)+|/[0-9]*-*of\\ emotes(?=\\W|$)+'
-            '|/[0-9]*-*sender\\ of(?=\\W|$)+|/[0-9]*-*A\\ nice(?=\\W|$)+|/[0-9]*-*sender(?=\\W|$)+'
-            '|/[0-9]*-*emotes(?=\\W|$)+|/[0-9]*-*nice(?=\\W|$)+|/[0-9]*-*of(?=\\W|$)+|/[0-9]*-*A(?=\\W|$)+')
+            '/[0-9]*-*A\\ nice\\ sender\\ of\\ emotes(?=\\W|$)+|'
+            '/[0-9]*-*nice\\ sender\\ of\\ emotes(?=\\W|$)+|'
+            '/[0-9]*-*A\\ nice\\ sender\\ of(?=\\W|$)+|'
+            '/[0-9]*-*sender\\ of\\ emotes(?=\\W|$)+|'
+            '/[0-9]*-*nice\\ sender\\ of(?=\\W|$)+|'
+            '/[0-9]*-*A\\ nice\\ sender(?=\\W|$)+|'
+            '/[0-9]*-*nice\\ sender(?=\\W|$)+|'
+            '/[0-9]*-*of\\ emotes(?=\\W|$)+|'
+            '/[0-9]*-*sender\\ of(?=\\W|$)+|'
+            '/[0-9]*-*A\\ nice(?=\\W|$)+|'
+            '/[0-9]*-*emotes(?=\\W|$)+|'
+            '/[0-9]*-*sender(?=\\W|$)+|'
+            '/[0-9]*-*nice(?=\\W|$)+|'
+            '/[0-9]*-*of(?=\\W|$)+|'
+            '/[0-9]*-*A(?=\\W|$)+'
+            )
 
     def test_sdesc_handler(self):
         self.speaker.sdesc.add(sdesc0)
@@ -122,9 +132,13 @@ class TestRPSystem(EvenniaTest):
         self.speaker.sdesc.add("Testing three words")
         self.assertEqual(
             self.speaker.sdesc.get_regex_tuple()[0].pattern,
-            '/[0-9]*-*Testing\\ three\\ words(?=\\W|$)+|/[0-9]*-*Testing\\ '
-            'three(?=\\W|$)+|/[0-9]*-*three\\ words(?=\\W|$)+|/[0-9]*-*Testing'
-            '(?=\\W|$)+|/[0-9]*-*three(?=\\W|$)+|/[0-9]*-*words(?=\\W|$)+')
+            '/[0-9]*-*Testing\ three\ words(?=\W|$)+|'
+            '/[0-9]*-*Testing\ three(?=\W|$)+|'
+            '/[0-9]*-*three\ words(?=\W|$)+|'
+            '/[0-9]*-*Testing(?=\W|$)+|'
+            '/[0-9]*-*three(?=\W|$)+|'
+            '/[0-9]*-*words(?=\W|$)+'
+            )
 
     def test_recog_handler(self):
         self.speaker.sdesc.add(sdesc0)