diff --git a/src/calibre/devices/usbms/driver.py b/src/calibre/devices/usbms/driver.py
index ae5504fc71..5c5a7fb1da 100644
--- a/src/calibre/devices/usbms/driver.py
+++ b/src/calibre/devices/usbms/driver.py
@@ -10,9 +10,11 @@ for a particular device.
 import os
 import fnmatch
 import shutil
+from math import ceil
 from itertools import cycle
 
 from calibre import sanitize_file_name as sanitize
+from calibre.constants import iswindows
 from calibre.ebooks.metadata import authors_to_string
 from calibre.devices.usbms.cli import CLI
 from calibre.devices.usbms.device import Device
@@ -127,6 +129,7 @@ class USBMS(CLI, Device):
 
         for i, infile in enumerate(files):
             newpath = path
+            resizable = []
 
             if self.SUPPORTS_SUB_DIRS:
                 mdata = metadata.next()
@@ -135,23 +138,54 @@ class USBMS(CLI, Device):
                     for tag in mdata['tags']:
                         if tag.startswith(_('News')):
                             newpath = os.path.join(newpath, 'news')
-                            newpath = os.path.join(newpath, sanitize(mdata.get('title', '')))
-                            newpath = os.path.join(newpath, sanitize(mdata.get('timestamp', '')))
+                            c = sanitize(mdata.get('title', ''))
+                            if c:
+                                newpath = os.path.join(newpath, c)
+                                resizable.append(c)
+                            c = sanitize(mdata.get('timestamp', ''))
+                            if c:
+                                newpath = os.path.join(newpath, c)
+                                resizable.append(c)
                             break
                         elif tag.startswith('/'):
-                            newpath += tag
-                            newpath = os.path.normpath(newpath)
+                            for c in tag.split('/'):
+                                c = sanitize(c)
+                                if not c: continue
+                                newpath = os.path.join(newpath, c)
+                                resizable.append(c)
                             break
 
                 if newpath == path:
-                    newpath = os.path.join(newpath,
-                        sanitize(mdata.get('authors', _('Unknown'))),
-                        sanitize(mdata.get('title', _('Unknown'))))
+                    c = sanitize(mdata.get('authors', _('Unknown')))
+                    if c:
+                        newpath = os.path.join(newpath, c)
+                        resizable.append(c)
+                    c = sanitize(mdata.get('title', _('Unknown')))
+                    if c:
+                        newpath = os.path.join(newpath, c)
+                        resizable.append(c)
+
+            newpath = os.path.abspath(newpath)
+            fname = sanitize(names.next())
+            resizable.append(fname)
+            filepath = os.path.join(newpath, fname)
+
+            if iswindows and len(filepath) > 250:
+                extra = len(filepath) - 250
+                delta = int(ceil(extra/float(len(resizable))))
+                for x in resizable:
+                    if delta > len(x):
+                        r = ''
+                    else:
+                        r = x[:-delta]
+                    filepath = filepath.replace(os.sep+x+os.sep, os.sep+r+os.sep)
+                filepath = filepath.replace(os.sep+os.sep, os.sep)
+                newpath = os.path.dirname(filepath)
+
 
             if not os.path.exists(newpath):
                 os.makedirs(newpath)
 
-            filepath = os.path.join(newpath, sanitize(names.next()))
             paths.append(filepath)
 
             if hasattr(infile, 'read'):