Microsoft has been playing a rather interesting game lately in regard to where you will find some of its services and programs.

On Facebook you will find that Messenger is one of the most popular apps. Bing has found its way onto iOS via the iPhone and iPad, and now you can get a Hotmail email app for Android.

Also, we are seeing a constant flow of improvements for programs, both new and old, as Microsoft continues to re-image itself.

The latest service slated to be improved is Hotmail, and in an interview with WinRumors last week Mark West from Microsoft had this to say about Hotmail:

 “We really kind of lost our way a little bit,” […] “Gmail came out, they were doing some great stuff especially around storage and they were really being very disruptive and got an awful lot of traction off the back of that.”

Don’t get me wrong, this is great news. I love the fact that Microsoft is getting its mojo back and that Hotmail is finally getting the serious attention it needs, however it isn’t just the lack of features that is the biggest problem facing Hotmail.

The biggest hurdle facing Hotmail going forward: Its name.

Hotmail is a great name in of itself, rather it is the association of it with the Microsoft of old, the evil empire, the soul crusher from Redmond. It also doesn’t help that Hotmail has been synonymous for years with spam and malware.

As Matthew O’Day, Hotmail Program Manager, wrote in a recent blog post:

At the same time, we understand that there’s still a perception that Hotmail is slow, spammy, lacking on storage – essentially outdated.

We looked at that as a challenge. Why not go above and beyond to not only fix the pain points but create an inbox that feels like a true upgrade compared to the others out there?

It is one thing to pump some life into Hotmail and make it a true modern web email client that can very possibly give Gmail a run for the money, but that is a far cry from making it cool. It is going to be  a long haul to make a Hotmail account an email address that isn’t used as a throw-away instead of a primary contact point.  Feature improvement is a good starting point, but Hotmail also needs a complete PR makeover.  That will most likely be the larger challenge as Hotmail strives to compete with Gmail.

[Cross-posted at Winextra]