diff --git a/game/scripts/doll/clothes_dynamic.rpy b/game/scripts/doll/clothes_dynamic.rpy
index f97d7d73..4b9c24f6 100644
--- a/game/scripts/doll/clothes_dynamic.rpy
+++ b/game/scripts/doll/clothes_dynamic.rpy
@@ -1,6 +1,6 @@
 init python:
     class DollClothDynamic(DollCloth):
-        prefixes = ["!=", "?=", "+=", "!", "?", "+"]
+        prefixes = ["!=", "?=", "+=", "!", "?", "+", "*"]
 
         def __init__(self, name, categories, type, id, color, zorder=None, unlocked=False, level=0, blacklist=[], modpath=None, tracking=None, parent=None):
             self._tracking = tracking
@@ -21,7 +21,7 @@ init python:
 
         @property
         def tracking_object(self):
-            if self.prefix in ("!", "?", "+"):
+            if self.prefix in ("!", "?", "+", "*"):
                 return self.char.states.get(self.tracking)[0]
             else:
                 return eval(self.tracking)
@@ -49,6 +49,18 @@ init python:
                     return "default"
                 return tracking_id
 
+            def _lookahead_type(path):
+                tracking_object = self.tracking_object
+
+                if not tracking_object:
+                    return "default"
+
+                path = posixpath.join(path, tracking_object.type)
+
+                if not any(fp.startswith(path) for fp in renpy.list_files()):
+                    return "default"
+                return tracking_object.type
+
             def _chainload():
 
                 def __wrapper(obj):
@@ -89,6 +101,7 @@ init python:
                     "!": lambda tracking, _: _negative_lookahead(),
                     "?": lambda tracking, path: _lookahead(path),
                     "+": lambda tracking, _: _chainload(),
+                    "*": lambda tracking, path: _lookahead_type(path),
                     "!=": lambda tracking, _: _negative_lookahead_item(),
                     "?=": lambda tracking, _: _lookahead_item(),
                     "+=": lambda tracking, _: _chainload(),
diff --git a/game/scripts/doll/main.rpy b/game/scripts/doll/main.rpy
index e009b85c..32ed62ad 100644
--- a/game/scripts/doll/main.rpy
+++ b/game/scripts/doll/main.rpy
@@ -235,16 +235,24 @@ init python:
         def unequip(self, *args):
             """Takes argument(s) containing string cloth type(s) to unequip."""
 
+            def _tracker_rebuild(type):
+                for tracking in self.get_trackers_list(type):
+                    tracking.is_stale()
+
             def _unequip_all():
                 for k, v in self.states.items():
                     if not k in self.blacklist_unequip:
                         v[0], v[2] = None, True
 
+                        _tracker_rebuild(k)
+
             def _unequip_type(type):
                 for k, v in self.states.items():
                     if not k in self.blacklist_unequip and istype(v[0], type):
                         v[0], v[2] = None, True
 
+                        _tracker_rebuild(k)
+
             def _unequip_slot(slot):
                 if slot in self.blacklist_unequip:
                     return
@@ -256,6 +264,8 @@ init python:
                 else:
                     self.states[slot][0], self.states[slot][2] = None, True
 
+                _tracker_rebuild(slot)
+
             for arg in args:
                 if isinstance(arg, str):
                     if arg == "all":
@@ -302,16 +312,24 @@ init python:
 
         def strip(self, *args):
             """Takes argument(s) containing string cloth type(s) to temporarily displace (hide)."""
+            def _tracker_rebuild(type):
+                for tracking in self.get_trackers_list(type):
+                    tracking.is_stale()
+
             def _strip_all():
                 for k, v in self.states.items():
                     if not k.startswith(self.blacklist_unequip):
                         v[2] = False
 
+                        _tracker_rebuild(k)
+
             def _strip_type(type):
                 for k, v in self.states.items():
                     if istype(v[0], type) and not k in self.blacklist_unequip and (k in self.multislots or not k.startswith(self.blacklist_strip)):
                         v[2] = False
 
+                        _tracker_rebuild(k)
+
             def _strip_slot(slot):
                 if slot in self.blacklist_unequip:
                     return
@@ -323,6 +341,8 @@ init python:
                 else:
                     self.states[slot][2] = False
 
+                _tracker_rebuild(slot)
+
             for arg in args:
 
                 if arg == "all":
@@ -342,15 +362,23 @@ init python:
 
         def wear(self, *args):
             """Takes argument(s) containing string cloth type(s) to temporarily displace (hide)."""
+            def _tracker_rebuild(type):
+                for tracking in self.get_trackers_list(type):
+                    tracking.is_stale()
+
             def _wear_all():
                 for k, v in self.states.items():
                     v[2] = True
 
+                    _tracker_rebuild(k)
+
             def _wear_type(type):
                 for k, v in self.states.items():
                     if istype(v[0], type):
                         v[2] = True
 
+                        _tracker_rebuild(v)
+
             def _wear_slot(slot):
                 if slot in self.multislots:
                     for k, v in self.states.items():
@@ -359,6 +387,8 @@ init python:
                 else:
                     self.states[slot][2] = True
 
+                _tracker_rebuild(slot)
+
             for arg in args:
 
                 if arg == "all":
diff --git a/game/scripts/utility/devtools.rpy b/game/scripts/utility/devtools.rpy
index 74e5ab4b..7f1d6868 100644
--- a/game/scripts/utility/devtools.rpy
+++ b/game/scripts/utility/devtools.rpy
@@ -26,26 +26,25 @@ python early:
         UNDERLINE = '\033[4;37;48m'
         END = '\033[1;37;0m'
 
-    if config.developer:
-        # Debug
+    # Debug
+    # Note: config.developer flag is set to False during early initialisation
+    def detect_orphaned_rpyc_files():
+        excluded = ["tl/", "00db.rpyc", "00sshtransition.rpyc"]
 
-        def detect_orphaned_rpyc_files():
-            excluded = ["tl/"]
+        files = renpy.list_files(common=True)
 
-            files = renpy.list_files(common=True)
-            compiled = [x for x in files if x.endswith(".rpyc") if not any(x.startswith(i) for i in excluded)]
-            scripts = [x for x in files if x.endswith(".rpy")]
-            orphaned = []
+        compiled = [x for x in files if x.endswith(".rpyc") if not any(x.startswith(i) for i in excluded)]
+        scripts = [x for x in files if x.endswith(".rpy")]
+        orphaned = []
 
-            for i in compiled:
-                if not i[:-1] in scripts:
-                    orphaned.append(i)
+        for i in compiled:
+            if not i[:-1] in scripts:
+                orphaned.append(i)
 
-            if orphaned:
-                raise Exception(f"Orphaned compiled scripts detected, please delete them before continuing:\n{orphaned}")
-
-        detect_orphaned_rpyc_files()
+        if orphaned:
+            raise Exception(f"Orphaned compiled scripts detected, please force recompile in Ren'py Launcher before continuing:\n{orphaned}")
 
+    detect_orphaned_rpyc_files()
 
     # class InstanceDebugger(object):