diff --git a/beets/dbcore/query.py b/beets/dbcore/query.py
index 14117f9af..39ff0dc77 100644
--- a/beets/dbcore/query.py
+++ b/beets/dbcore/query.py
@@ -148,6 +148,8 @@ class MatchQuery(FieldQuery):
 
 
 class NoneQuery(FieldQuery):
+    """A query that checks whether a field is null."""
+
     def __init__(self, field, fast=True):
         super(NoneQuery, self).__init__(field, None, fast)
 
diff --git a/beetsplug/web/__init__.py b/beetsplug/web/__init__.py
index 290f25b48..635c2f5a8 100644
--- a/beetsplug/web/__init__.py
+++ b/beetsplug/web/__init__.py
@@ -217,12 +217,20 @@ def all_items():
 @app.route('/item/<int:item_id>/file')
 def item_file(item_id):
     item = g.lib.get_item(item_id)
+
+    # On Windows under Python 2, Flask wants a Unicode path. On Python 3, it
+    # *always* wants a Unicode path.
+    if os.name == 'nt':
+        item_path = util.syspath(item.path)
+    else:
+        item_path = util.py3_path(item.path)
+
     response = flask.send_file(
-        util.py3_path(item.path),
+        item_path,
         as_attachment=True,
         attachment_filename=os.path.basename(util.py3_path(item.path)),
     )
-    response.headers['Content-Length'] = os.path.getsize(item.path)
+    response.headers['Content-Length'] = os.path.getsize(item_path)
     return response
 
 
diff --git a/docs/changelog.rst b/docs/changelog.rst
index 299d380f9..b3bee8a44 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -28,6 +28,8 @@ Fixes:
 * :doc:`/plugins/lastgenre`: Fix a crash when using the `prefer_specific` and
   `canonical` options together. Thanks to :user:`yacoob`. :bug:`2459`
   :bug:`2583`
+* :doc:`/plugins/web`: Fix a crash on Windows under Python 2 when serving
+  non-ASCII filenames. Thanks to :user:`robot3498712`. :bug:`2592` :bug:`2593`
 
 
 1.4.4 (June 10, 2017)