diff --git a/src/calibre/utils/localunzip.py b/src/calibre/utils/localunzip.py
index 8b2b2f58b4..8af2cd736b 100644
--- a/src/calibre/utils/localunzip.py
+++ b/src/calibre/utils/localunzip.py
@@ -33,6 +33,20 @@ LocalHeader = namedtuple('LocalHeader',
         'filename extra')
 
 
+if hasattr(sys, 'getwindowsversion'):
+    windows_reserved_filenames = (
+        'CON', 'PRN', 'AUX', 'CLOCK$', 'NUL' 'COM0', 'COM1', 'COM2', 'COM3',
+        'COM4', 'COM5', 'COM6', 'COM7', 'COM8', 'COM9' 'LPT0', 'LPT1', 'LPT2',
+        'LPT3', 'LPT4', 'LPT5', 'LPT6', 'LPT7', 'LPT8', 'LPT9')
+
+    def is_reserved_filename(x):
+        base = x.partition('.')[0].upper()
+        return base in windows_reserved_filenames
+else:
+    def is_reserved_filename(x):
+        return False
+
+
 def decode_arcname(name):
     if isinstance(name, bytes):
         from calibre.ebooks.chardet import detect
@@ -207,11 +221,18 @@ def _extractall(f, path=None, file_info=None):
             if not os.path.exists(bdir):
                 os.makedirs(bdir)
             dest = os.path.join(path, *parts)
-            with open(dest, 'wb') as o:
+            try:
+                df = open(dest, 'wb')
+            except EnvironmentError:
+                if is_reserved_filename(os.path.basename(dest)):
+                    raise ValueError('This ZIP file contains a file with a reserved filename'
+                            ' that cannot be processed on Windows: {}'.format(os.path.basename(dest)))
+                raise
+            with df:
                 if header.compression_method == ZIP_STORED:
-                    copy_stored_file(f, header.compressed_size, o)
+                    copy_stored_file(f, header.compressed_size, df)
                 else:
-                    copy_compressed_file(f, header.compressed_size, o)
+                    copy_compressed_file(f, header.compressed_size, df)
         else:
             f.seek(f.tell()+seekval)