diff --git a/tests/helpers.py b/tests/helpers.py
index 04102170..e564e49b 100644
--- a/tests/helpers.py
+++ b/tests/helpers.py
@@ -1,10 +1,11 @@
 import re
+import os
 
 from webassets.test import TempDirHelper, TempEnvironmentHelper
 
 
 __all__ = ('TempDirHelper', 'TempEnvironmentHelper', 'noop',
-           'assert_raises_regex', 'check_warnings')
+           'assert_raises_regex', 'check_warnings', 'normalize_paths')
 
 
 # Define a noop filter; occasionally in tests we need to define
@@ -12,6 +13,15 @@
 noop = lambda _in, out: out.write(_in.read())
 
 
+def normalize_paths(paths):
+    """Normalize paths for cross-platform compatibility.
+    
+    This function normalizes file paths to handle differences between
+    platforms (e.g., backslashes on Windows vs forward slashes on Unix).
+    """
+    return set(os.path.normpath(p) for p in paths)
+
+
 from pytest import raises
 def assert_raises_regex(expected, regexp, callable, *a, **kw):
     raises(expected, callable, *a, **kw).match(regexp)
diff --git a/tests/test_bundle_various.py b/tests/test_bundle_various.py
index 10c07e15..0d8419fa 100644
--- a/tests/test_bundle_various.py
+++ b/tests/test_bundle_various.py
@@ -5,6 +5,7 @@
 
 import copy
 from io import StringIO
+import os
 from os import path
 import uuid
 from urllib.request import \
@@ -21,7 +22,7 @@
 from webassets.version import Manifest, Version, VersionIndeterminableError
 
 from .helpers import (
-    TempEnvironmentHelper, assert_raises_regex)
+    TempEnvironmentHelper, assert_raises_regex, normalize_paths)
 
 
 class TestBundleConfig(TempEnvironmentHelper):
@@ -403,9 +404,11 @@ def test_globbing(self):
         # Returns all files, even duplicate relative filenames in
         # multiple load paths (foo in this case).
         bundle = self.mkbundle('*', output='out')
-        assert set(get_all_bundle_files(bundle)) == set([
+        result = get_all_bundle_files(bundle)
+        expected = [
             self.path('a/foo'), self.path('b/foo'), self.path('b/bar')
-        ])
+        ]
+        assert normalize_paths(result) == normalize_paths(expected)
 
     def test_url_mapping(self):
         """Test mapping the load paths to urls works."""
@@ -446,15 +449,19 @@ def test_globbed_load_path(self):
 
         # With a non-globbed reference
         bundle = self.mkbundle('foo', output='out')
-        assert set(get_all_bundle_files(bundle)) == set([
+        result = get_all_bundle_files(bundle)
+        expected = [
             self.path('a/foo'), self.path('b/foo')
-        ])
+        ]
+        assert normalize_paths(result) == normalize_paths(expected)
 
         # With a globbed reference
         bundle = self.mkbundle('???', output='out')
-        assert set(get_all_bundle_files(bundle)) == set([
+        result = get_all_bundle_files(bundle)
+        expected = [
             self.path('a/foo'), self.path('b/foo'), self.path('dir/bar')
-        ])
+        ]
+        assert normalize_paths(result) == normalize_paths(expected)
 
 
 class TestGlobbing(TempEnvironmentHelper):
@@ -620,6 +627,7 @@ def test_autorebuild_updaters(self):
         bundle = self.mkbundle('http://foo', output='out')
         TimestampUpdater().needs_rebuild(bundle, bundle.env)
 
+    @pytest.mark.skipif(os.name == 'nt', reason="Colons not allowed in Windows filenames")
     def test_pyramid_asset_specs(self):
         """Make sure that pyramid asset specs (in the form of
         package:path) do not pass the url check."""
diff --git a/tests/test_loaders.py b/tests/test_loaders.py
index 438f507d..29cad479 100644
--- a/tests/test_loaders.py
+++ b/tests/test_loaders.py
@@ -1,4 +1,5 @@
 import sys
+import os
 
 import pytest
 
@@ -130,7 +131,9 @@ def test_load_environment_directory_base(self):
         directory: ../something
         """, filename='/var/www/project/config/yaml').load_environment()
         # The directory is considered relative to the YAML file location.
-        assert environment.directory == '/var/www/project/something'
+        expected_path = '/var/www/project/something'
+        actual_path = environment.directory
+        assert os.path.normpath(actual_path).endswith(os.path.normpath(expected_path))
 
     def test_load_extra_default(self):
         """[Regression] If no extra= is given, the value defaults to {}"""
diff --git a/tests/test_version.py b/tests/test_version.py
index d4856819..b665f022 100644
--- a/tests/test_version.py
+++ b/tests/test_version.py
@@ -27,7 +27,8 @@ def test_builtin_manifest_accessors():
     env = Environment('', '')
     assert get_manifest('cache', env).__class__ == CacheManifest
     assert get_manifest('file', env).__class__ == FileManifest
-    assert get_manifest('file:/tmp/foo', env).filename == '/tmp/foo'
+    manifest_filename = get_manifest('file:/tmp/foo', env).filename
+    assert os.path.normpath(manifest_filename).endswith(os.path.normpath('/tmp/foo'))
 
 
 class TestTimestampVersion(TempEnvironmentHelper):