diff --git a/voussoirkit/downloady.py b/voussoirkit/downloady.py
index e59b6bf..a1134b7 100644
--- a/voussoirkit/downloady.py
+++ b/voussoirkit/downloady.py
@@ -6,8 +6,9 @@ import urllib
 import warnings
 
 from voussoirkit import bytestring
-from voussoirkit import ratelimiter
 from voussoirkit import clipext
+from voussoirkit import pathclass
+from voussoirkit import ratelimiter
 from voussoirkit import safeprint
 
 warnings.simplefilter('ignore')
@@ -25,6 +26,11 @@ TEMP_EXTENSION = '.downloadytemp'
 
 PRINT_LIMITER = ratelimiter.Ratelimiter(allowance=5, mode='reject')
 
+SPECIAL_FILENAMES = [os.devnull]
+if os.name == 'nt':
+    SPECIAL_FILENAMES.append('con')
+SPECIAL_FILENAMES = [os.path.normcase(x) for x in SPECIAL_FILENAMES]
+
 class NotEnoughBytes(Exception):
     pass
 
@@ -50,7 +56,8 @@ def download_file(
     if os.path.isdir(localname):
         localname = os.path.join(localname, basename_from_url(url))
     localname = sanitize_filename(localname)
-    if localname != os.devnull:
+
+    if not is_special_file(localname):
         localname = os.path.abspath(localname)
 
     if verbose:
@@ -80,7 +87,10 @@ def download_plan(plan):
     directory = os.path.split(localname)[0]
     if directory != '':
         os.makedirs(directory, exist_ok=True)
-    touch(localname)
+
+    if not is_special_file(localname):
+        touch(localname)
+
     if plan['plan_type'] in ['resume', 'partial']:
         file_handle = open(localname, 'r+b')
         file_handle.seek(plan['seek_to'])
@@ -124,8 +134,8 @@ def download_plan(plan):
 
     file_handle.close()
 
-    # Don't try to rename /dev/null
-    if os.devnull not in [localname, plan['real_localname']]:
+    # Don't try to rename /dev/null or other special names
+    if not is_special_file(localname) and not is_special_file(plan['real_localname']):
         localsize = os.path.getsize(localname)
         undersized = plan['plan_type'] != 'partial' and localsize < plan['remote_total_bytes']
         if plan['raise_for_undersized'] and undersized:
@@ -155,12 +165,16 @@ def prepare_plan(
     headers = headers or {}
     user_provided_range = 'range' in headers
     real_localname = localname
-    temp_localname = localname + TEMP_EXTENSION
+    if is_special_file(localname):
+        temp_localname = localname
+    else:
+        temp_localname = localname + TEMP_EXTENSION
     real_exists = os.path.exists(real_localname)
 
     if real_exists and overwrite is False and not user_provided_range:
         print('File exists and overwrite is off. Nothing to do.')
         return None
+
     temp_exists = os.path.exists(temp_localname)
     real_localsize = int(real_exists and os.path.getsize(real_localname))
     temp_localsize = int(temp_exists and os.path.getsize(temp_localname))
@@ -349,6 +363,9 @@ def get_permission(prompt='y/n\n>', affirmative=['y', 'yes']):
     permission = input(prompt)
     return permission.lower() in affirmative
 
+def is_special_file(filename):
+    return os.path.normcase(filename) in SPECIAL_FILENAMES
+
 def request(method, url, stream=False, headers=None, timeout=TIMEOUT, verify_ssl=True, **kwargs):
     if headers is None:
         headers = {}