Windows Live Hotmail is not a hybrid of the original Windows Live Mail, as it was developed under the Windows Live umbrella brand, and MSN Hotmail. Windows Live Mail was in fact designed from scratch to replace Hotmail, and Microsoft simply acted up on user feedback with a rebranding in early 2007. Ellie Powers, program manager, Windows Live Hotmail, explained in detail the company's move from MSN to Windows Live Hotmail. This is one of the questions answered by Powers related to Windows Live Hotmail. There are five additional explanations on top of the information made available about the transition from MSN to Windows Live Hotmail.

One of the biggest issues with users is data loss. Microsoft has been receiving reports of the users' emails having disappeared from their inboxes. "Our support team has done a lot of investigation into these issues, and nearly every case is due to account expiration. Free Hotmail accounts expire if you haven’t logged into Hotmail for a certain number of days, which is a standard practice for web-based mail accounts because many users use an account for a little while, and then never use it again. MSN Hotmail accounts expire after 60 days, and Windows Live Hotmail accounts expire after 120 days. Advances in our data center have allowed us to extend our expiration times, which used to be 30 days", Powers said.

According to Microsoft, Windows Live Hotmail performance is always a top issue. In this context, the company is offering users the possibility to switch back to the classic version of the email service. In terms of speed, the latest version is also the fastest, but users have to wait for a healthy volume of JavaScript to download at the beginning. During the initial stages, the service may appear sluggish, especially over slow connections. Powers also advised users that failed to take a shine to the new AJAX-based graphical interface of Windows Live Hotmail to switch to the classic version. On top of this, Powers also admitted compatibility problems with the Safari browser.

"We added support for browsers other than Internet Explorer (IE) in 2005, and the non-IE browser we support best is Firefox 1.5+. It’s available for practically every operating system out there, so if you can’t use IE or don’t like it, try Firefox because it works well with a wide range of websites. We currently do not support the full version for Safari due to technical limitations, though we continue to monitor the issue. Safari users can use the classic version of Hotmail for now, and we are monitoring whether future versions of Safari will support all of our technical needs. As far as I know, there are only four features that IE supports but Firefox doesn’t", she explained.