Nick,
Yes.
If the CuteEditor security policy file, you find the following setting:
<security name="OverWriteExistingUploadedFile">false</security>
If the file is already available when uploading, CuteEditor won't allow the file is uploaded.
You can set it to true if you want to disable this feature.
asp.net Chat http://cutesoft.net/ASP.NET+Chat/default.aspx
Web Messenger: http://cutesoft.net/Web-Messenger/default.aspx
asp.net wysiwyg editor: http://cutesoft.net/ASP.NET+WYSIWYG+Editor/default.aspx
asp wysiwyg html editor: http://cutesoft.net/ASP
asp.net Image Gallery: http://cutesoft.net/ASP.NET+Image+Gallery/default.aspx
Live Support: http://cutesoft.net/live-support/default.aspx