I am using Windows Live Mail 2011 on a Windows 7 32bit machine. I have it configured with a pop3 account that is not a Microsoft account and it works fine for the most part. When I try to send a message from a 3rd party app with an attachment it asks for the Windows Live login. I don't use a Microsoft mail account so there is no way to login but it won't let me send a message this way. If I create a message out of Windows Live Mail 2011 with an attachment it works fine. Just not when I use a 3rd party app and an attachment. If I send a message without an attachment I have no issues.