diff --git a/client/ayon_core/host/interfaces/workfiles.py b/client/ayon_core/host/interfaces/workfiles.py
index 193d59322b..b6c33337e9 100644
--- a/client/ayon_core/host/interfaces/workfiles.py
+++ b/client/ayon_core/host/interfaces/workfiles.py
@@ -1113,11 +1113,6 @@ class IWorkfileHost:
             filepath = os.path.join(workdir, filename)
 
             rootless_path = f"{rootless_workdir}/{filename}"
-            # Double slashes can happen when root leads to root of disk or
-            #   when task exists on root folder
-            #   - '/{hierarchy}/{folder[name]}' -> '//some_folder'
-            while "//" in rootless_path:
-                rootless_path = rootless_path.replace("//", "/")
             workfile_entity = workfile_entities_by_path.pop(
                 rootless_path, None
             )
diff --git a/client/ayon_core/lib/path_templates.py b/client/ayon_core/lib/path_templates.py
index 9e3e455a6c..c6e9e14eac 100644
--- a/client/ayon_core/lib/path_templates.py
+++ b/client/ayon_core/lib/path_templates.py
@@ -3,6 +3,7 @@ import re
 import copy
 import numbers
 import warnings
+import platform
 from string import Formatter
 import typing
 from typing import List, Dict, Any, Set
@@ -12,6 +13,7 @@ if typing.TYPE_CHECKING:
 
 SUB_DICT_PATTERN = re.compile(r"([^\[\]]+)")
 OPTIONAL_PATTERN = re.compile(r"(<.*?[^{0]*>)[^0-9]*?")
+_IS_WINDOWS = platform.system().lower() == "windows"
 
 
 class TemplateUnsolved(Exception):
@@ -277,8 +279,11 @@ class TemplateResult(str):
         """Convert to normalized path."""
 
         cls = self.__class__
+        path = str(self)
+        if _IS_WINDOWS:
+            path = path.replace("\\", "/")
         return cls(
-            os.path.normpath(self.replace("\\", "/")),
+            os.path.normpath(path),
             self.template,
             self.solved,
             self.used_values,
diff --git a/client/ayon_core/pipeline/anatomy/templates.py b/client/ayon_core/pipeline/anatomy/templates.py
index d89b70719e..e3ec005089 100644
--- a/client/ayon_core/pipeline/anatomy/templates.py
+++ b/client/ayon_core/pipeline/anatomy/templates.py
@@ -1,6 +1,7 @@
 import os
 import re
 import copy
+import platform
 import collections
 import numbers
 
@@ -15,6 +16,7 @@ from .exceptions import (
     AnatomyTemplateUnsolved,
 )
 
+_IS_WINDOWS = platform.system().lower() == "windows"
 _PLACEHOLDER = object()
 
 
@@ -526,6 +528,14 @@ class AnatomyTemplates:
             root_key = "{" + root_key + "}"
             output = output.replace(str(used_value), root_key)
 
+        # Make sure rootless path is with forward slashes
+        if _IS_WINDOWS:
+            output.replace("\\", "/")
+
+        # Make sure there are no double slashes
+        while "//" in output:
+            output = output.replace("//", "/")
+
         return output
 
     def format(self, data, strict=True):