diff --git a/send2trash/plat_win.py b/send2trash/plat_win.py
index 5e50801..372fba7 100644
--- a/send2trash/plat_win.py
+++ b/send2trash/plat_win.py
@@ -7,7 +7,8 @@
 from __future__ import unicode_literals
 
 from ctypes import (windll, Structure, byref, c_uint,
-                    create_unicode_buffer, addressof)
+                    create_unicode_buffer, addressof,
+                    GetLastError, FormatError)
 from ctypes.wintypes import HWND, UINT, LPCWSTR, BOOL
 import os.path as op
 
@@ -49,6 +50,11 @@ def get_short_path_name(long_name):
     if not long_name.startswith('\\\\?\\'):
         long_name = '\\\\?\\' + long_name
     buf_size = GetShortPathNameW(long_name, None, 0)
+    # FIX: https://github.com/hsoft/send2trash/issues/31
+    # If buffer size is zero, an error has occurred.
+    if not buf_size:
+        err_no = GetLastError()
+        raise WindowsError(err_no, FormatError(err_no), long_name[4:])
     output = create_unicode_buffer(buf_size)
     GetShortPathNameW(long_name, output, buf_size)
     return output.value[4:]  # Remove '\\?\' for SHFileOperationW
@@ -83,4 +89,4 @@ def send2trash(path):
     fileop.lpszProgressTitle = None
     result = SHFileOperationW(byref(fileop))
     if result:
-        raise WindowsError(None, None, path, result)
+        raise WindowsError(result, FormatError(result), path)
diff --git a/tests/test_plat_win.py b/tests/test_plat_win.py
index b7d1608..326e39c 100644
--- a/tests/test_plat_win.py
+++ b/tests/test_plat_win.py
@@ -1,5 +1,6 @@
 # coding: utf-8
 import os
+import shutil
 import sys
 import unittest
 from os import path as op
@@ -8,12 +9,37 @@ from tempfile import gettempdir
 from send2trash import send2trash as s2t
 
 
+@unittest.skipIf(sys.platform != 'win32', 'Windows only')
+class TestNormal(unittest.TestCase):
+    def setUp(self):
+        self.dirname = '\\\\?\\' + op.join(gettempdir(), 'python.send2trash')
+        self.file = op.join(self.dirname, 'testfile.txt')
+        self._create_tree(self.file)
+
+    def tearDown(self):
+        shutil.rmtree(self.dirname, ignore_errors=True)
+
+    def _create_tree(self, path):
+        dirname = op.dirname(path)
+        if not op.isdir(dirname):
+            os.makedirs(dirname)
+        with open(path, 'w') as writer:
+            writer.write('send2trash test')
+
+    def test_trash_file(self):
+        s2t(self.file)
+        self.assertFalse(op.exists(self.file))
+
+    def test_file_not_found(self):
+        file = op.join(self.dirname, 'otherfile.txt')
+        self.assertRaises(WindowsError, s2t, file)
+
 @unittest.skipIf(sys.platform != 'win32', 'Windows only')
 class TestLongPath(unittest.TestCase):
     def setUp(self):
         filename = 'A' * 100
-        self.dirname = '\\\\?\\' + os.path.join(gettempdir(), filename)
-        self.file = os.path.join(
+        self.dirname = '\\\\?\\' + op.join(gettempdir(), filename)
+        self.file = op.join(
             self.dirname,
             filename,
             filename,  # From there, the path is not trashable from Explorer
@@ -22,14 +48,11 @@ class TestLongPath(unittest.TestCase):
         self._create_tree(self.file)
 
     def tearDown(self):
-        try:
-            os.remove(self.dirname)
-        except OSError:
-            pass
+        shutil.rmtree(self.dirname, ignore_errors=True)
 
     def _create_tree(self, path):
-        dirname = os.path.dirname(path)
-        if not os.path.isdir(dirname):
+        dirname = op.dirname(path)
+        if not op.isdir(dirname):
             os.makedirs(dirname)
         with open(path, 'w') as writer:
             writer.write('Looong filename!')