Like a lot of people I paid attention when Microsoft updated Hotmail and declared war on Gmail. That’s a bold move and to pull it off they must be confident that the features they are delivering really are transformative… but having done it with Bing (love it, don’t use Google much at all anymore) I figured maybe they were on a roll.

Many commentators agree, saying Microsoft has delivered the goods with “quick views”, better attachment handling, a Gmail-like conversation view (which itself is nothing new, many wonder why it took them so long to do this), and more. I thought I would revisit my old friend, having not used anything other than Gmail (for public email) since 2004.

For whatever reason my old hotmail email address is no longer available (which kind of pissed me off because I had jnolan@), having been subsumed by my Live.com account which, ironically, is my jnolan at gmail dot com email. When signing into my Live.com account and clicking on the “mail” tab I am told I don’t have a mailbox and must create one. There doesn’t appear to be any way to get to Hotmail other than going through the Live.com frontend.

I understand that it is pretty difficult for a Live.com account identified by my GMail address to have a corresponding email account via Hotmail, but I have to wonder why the hell nobody thought about this back when they were building the Live.com identity system? It’s not like Live.com predates Hotmail. While mildly annoyed that I must create a new inbox I figure it’s no big deal so I click on the sign me up button.

Upon clicking the “sign me up” button I am presented with yet another roadblock, this time telling me it could not sign me out of Live.com to move on to the Hotmail new account creation workflow. Furthermore, it’s telling me I have to enable cookies but I know for fact that I have cookies enabled so now I am at a roadblock which after investing the time to get this far I am not willing to go farther. No new Hotmail account for me, moving on and not going to bother trying again. #FAIL.

I am not writing about this to beat up on Microsoft although I think they deserve it for creating that maddening Live.com identity system with inherent and intractable conflicts with how Hotmail handles identity, but rather to point out that consumer online services have a very fragile relationship with new users where every single interaction adds or detracts from the experience and when it breaks you have lost that user forever. When you get me and build up a track record I am willing to put up some hassle because I have invested time in the relationship, as is the case with Gmail and performance at the moment, but when we are just starting the relationship is more like speed dating, you get 5 minutes to impress me or I move on. Microsoft, you wasted your 5 minutes with me.