diff --git a/test/test_web.py b/test/test_web.py
index a4c10a193..606f1e243 100644
--- a/test/test_web.py
+++ b/test/test_web.py
@@ -13,11 +13,22 @@ from test import _common
 from beets.library import Item, Album
 from beetsplug import web
 
+import platform
+
+from beets import logging
+
 
 class WebPluginTest(_common.LibTestCase):
 
     def setUp(self):
+
         super(WebPluginTest, self).setUp()
+        self.log = logging.getLogger('beets.web')
+
+        if platform.system() == 'Windows':
+            self.path_prefix = u'C:'
+        else:
+            self.path_prefix = u''
 
         # Add fixtures
         for track in self.lib.items():
@@ -26,23 +37,30 @@ class WebPluginTest(_common.LibTestCase):
         # Add library elements. Note that self.lib.add overrides any "id=<n>"
         # and assigns the next free id number.
         # The following adds will create items #1, #2 and #3
+        path1 = self.path_prefix + os.sep + \
+            os.path.join(b'path_1').decode('utf-8')
         self.lib.add(Item(title=u'title',
-                          path=os.sep + os.path.join('path_1'),
+                          path=path1,
                           album_id=2,
                           artist='AAA Singers'))
+        path2 = self.path_prefix + os.sep + \
+            os.path.join(b'somewhere', b'a').decode('utf-8')
         self.lib.add(Item(title=u'another title',
-                          path=os.sep + os.path.join('somewhere', 'a'),
+                          path=path2,
                           artist='AAA Singers'))
+        path3 = self.path_prefix + os.sep + \
+            os.path.join(b'somewhere', b'abc').decode('utf-8')
         self.lib.add(Item(title=u'and a third',
                           testattr='ABC',
-                          path=os.sep + os.path.join('somewhere', 'abc'),
+                          path=path3,
                           album_id=2))
         # The following adds will create albums #1 and #2
         self.lib.add(Album(album=u'album',
                            albumtest='xyz'))
+        path4 = self.path_prefix + os.sep + \
+            os.path.join(b'somewhere2', b'art_path_2').decode('utf-8')
         self.lib.add(Album(album=u'other album',
-                           artpath=os.sep
-                           + os.path.join('somewhere2', 'art_path_2')))
+                           artpath=path4))
 
         web.app.config['TESTING'] = True
         web.app.config['lib'] = self.lib
@@ -53,9 +71,11 @@ class WebPluginTest(_common.LibTestCase):
         web.app.config['INCLUDE_PATHS'] = True
         response = self.client.get('/item/1')
         res_json = json.loads(response.data.decode('utf-8'))
+        expected_path = self.path_prefix + os.sep \
+            + os.path.join(b'path_1').decode('utf-8')
 
         self.assertEqual(response.status_code, 200)
-        self.assertEqual(res_json['path'], os.path.join(os.sep, u'path_1'))
+        self.assertEqual(res_json['path'], expected_path)
 
         web.app.config['INCLUDE_PATHS'] = False
 
@@ -63,10 +83,11 @@ class WebPluginTest(_common.LibTestCase):
         web.app.config['INCLUDE_PATHS'] = True
         response = self.client.get('/album/2')
         res_json = json.loads(response.data.decode('utf-8'))
+        expected_path = self.path_prefix + os.sep \
+            + os.path.join(b'somewhere2', b'art_path_2').decode('utf-8')
 
         self.assertEqual(response.status_code, 200)
-        self.assertEqual(res_json['artpath'],
-                         os.path.join(os.sep, u'somewhere2', u'art_path_2'))
+        self.assertEqual(res_json['artpath'], expected_path)
 
         web.app.config['INCLUDE_PATHS'] = False
 
@@ -180,11 +201,14 @@ class WebPluginTest(_common.LibTestCase):
                          u'and a third')
 
     def test_query_item_path(self):
-        # """ testing item query: path:\somewhere """
+        # """ testing item query: path:\somewhere\a """
         """ Note: path queries are special: the query item must match the path
         from the root all the way to a directory, so this matches 1 item """
         """ Note: filesystem separators in the query must be '\' """
-        response = self.client.get('/item/query/path:\\somewhere\\a')
+
+        response = self.client.get('/item/query/path:'
+                                   + self.path_prefix
+                                   + '\\somewhere\\a')
         res_json = json.loads(response.data.decode('utf-8'))
 
         self.assertEqual(response.status_code, 200)