diff --git a/src/common/helpers.py b/src/common/helpers.py
index 0be1163f6..8c58f4491 100644
--- a/src/common/helpers.py
+++ b/src/common/helpers.py
@@ -170,6 +170,11 @@ def prep(user, server, resource):
 		else:
 			return server
 
+def windowsify(s):
+	if os.name == 'nt':
+		return s.capitalize()
+	return s
+
 def temp_failure_retry(func, *args, **kwargs):
 	while True:
 		try:
diff --git a/src/groupchat_control.py b/src/groupchat_control.py
index 4cecf8c97..fa8aacb1c 100644
--- a/src/groupchat_control.py
+++ b/src/groupchat_control.py
@@ -1271,8 +1271,10 @@ class GroupchatControl(ChatControlBase, GroupChatCommands):
 							os.path.join(path, puny_new_nick + ext)
 					for old_file in files:
 						if os.path.exists(old_file) and old_file != files[old_file]:
-							if os.path.exists(files[old_file]):
-								# Windows require this
+							if os.path.exists(files[old_file]) and helpers.windowsify(
+							old_file) != helpers.windowsify(files[old_file]):
+								# Windows require this, but os.remove('test') will also
+								# remove 'TEST'
 								os.remove(files[old_file])
 							os.rename(old_file, files[old_file])
 					self.print_conversation(s, 'info', tim)