Microsoft Tech Migrations Good, Bad and Ugly

Microsoft is suddenly moving very quickly to new technologies and leaving some users hurt and confused

Users of Microsoft technologies have found themselves in unfamiliar territory over the past year as the erstwhile software giant moves surprisingly quickly to replace old technology products and services with new ones. If you are a user or fan of such things as Zune, Windows Live Messenger, or Hotmail, you know what I’m talking about. And the level of pain you’re feeling is going to vary according to how well Microsoft manages those transition, and how well you can handle change.

Zune, Windows Live Messenger, and Hotmail aren’t the only examples of Microsoft technology transitions we’re currently undergoing—arguably, the hybrid Windows 8 OS is the poster child—but they’re timely and representative of the sweeping changes that are now shaking the Microsoft ecosystem to its core. If you’re used to thinking of Microsoft as slow-moving and behind the times, think again. Some of these transitions are going to be difficult.

In fact, we can neatly divide these three transitions into good, bad, and ugly. Since I hate to leave things on a down note, let’s do them in reverse order.

Ugly: Windows Live Messenger to Skype

Windows Live Messenger has evolved into a heavy pig of an instant messaging client with tons of superfluous features no one wants. But it’s core uses—text-based IM and file sharing—have never been less than excellent, and for the hundreds of millions of people who use it—including me, Mary Jo Foley, Rafael Rivera, and many others in the Microsoft sphere—it’s the go-to choice for quick interactions. And now it’s going away. And what Microsoft is replacing it with, the horrible Skype client, is even worse.

I’ve written about the mess Microsoft created—by allowing Skype to operate as an independent entity and by pushing Windows Live Messenger users, and all Messenger service users, to Skype whether it’s ready or not—in Microsoft Sticks a Skype-Shaped Dagger in Messenger. And I’ve tried the pragmatic approach by making this transition early myself and providing Skype Switcher Tip: Use Compact View to help others make the move. Truth is, it doesn’t work. Skype is simply not acceptable for IM, and it doesn’t play well with the Messenger network.

According to Microsoft, the transition is this easy:

1. Download Skype.

2. Sign in with your Microsoft account (same as your Messenger ID).

3. There is no step 3.

But it’s not, and anyone who actually tries to use Skype as a Messenger replacement will discover as I and others have, that things simply stop working behind the scenes. Your contacts disappear. You appear offline to them. Messages are never delivered. A train wreck, basically.

Skype offers a few places to go for help as well:

I used to use Messenger, what do I need to know about Skype for Windows desktop?

What happens when I merge my Skype and Microsoft accounts?

What happens to my contacts when I merge my Skype and Microsoft accounts?

Good luck.

Bad: Zune to Xbox Music

While Zune started off as a horrible, misguided mess with a weird reskinned version of Windows Media Player for a client and the strangest hubris-laden launch I’ve ever witnessed out of Redmond, it quickly settled down and became an excellent iPod/iTunes alternative. In fact, over each generation of Zune, there were decided advantages to the Microsoft platform when compared to Apple’s, including an excellent subscription music service, Zune Music Pass.

So while Zune’s adherents continue to cling desperately to the last vestiges of this dying platform, the Zune brand somehow emerged as a kind of joke to those who don’t know better. So Microsoft has replaced the brand with Xbox, and has replaced the entertainment services with the Xbox Music and Xbox Video services. As I’ve been documenting via Xbox Music Book and a series of Xbox Music feature focus articles, however, Xbox Music is a mess. And it’s going to be an ugly transition.

If you try to visit the Zune web site, you’ll be directed to a support/maintenance page on the Xbox web site, which has a link to download the Zune PC software (still required to sync Zune devices and Windows Phone 7.x handsets) as well as various FAQs, support, and account management facilities.

Good: Hotmail to Outlook.com

Of the three transitions noted here, this one is generally the easiest and is arguably even desirable. Starting immediately, Microsoft is transitioning Hotmail users to the new Outlook.com user experience, so you can wait until that happens or you can simply login to Outlook.com with your Hotmail (or Live.com or MSN.com) email address and start using it immediately. You won’t be disappointed: Except for the Calendar experience, which still looks and works like the old Hotmail version, Outlook.com is a beautiful, efficient solution for email and contacts management, and it’s one that I use every single day.

I’ve written a lot about the Outlook.com migration, but the obvious place for switchers to start is Outlook.com Tips.

If you’re looking to Microsoft for help, you should start with Outlook.com Support. Here, you’ll find answers to frequently asked questions about Mail and People, and a link to what is perhaps the most pertinent FAQ, My Hotmail account was upgraded to Outlook.com. You can also check to see whether everything’s running normally at Microsoft’s service status page.

Closing thoughts

We’re in brave new world territory here, there’s no doubt about it. Hopefully, with the passage of time, and new versions of the software and services we’re being pushed to whether we want it or not, the rough patches will be ironed out and we can move forward. Until that happens, expect a lot of complaining, though it’s worth noting that there are harder transitions awaiting some. Just wait until Windows XP drops off the face of the earth in April 2014. Now that one is going to be entertaining.

Discuss this Article 8

sege122
on Feb 22, 2013

I have always liked Skype. Never really used messenger much so it's no personal loss to me.

I used Hotmail before MS had it and I loved it. Microsoft didn't seem to care much about spam and the mail experience so I went off with Gmail. However Outlook.com is probably the best in class right now. I am migrating to mainly using Outlook.com and, with the skydrive integration for big files (thanks for the tip) it is at least as functional a solution as dropbox plus email.

Xbox Music is unbelievable. The Zune client with Windowsphone 7.x was a pretty functional beast for me. It was less bloat ridden than iTunes and the sync functionality was good. It was also an excellent music manager. It was even great for podcasts. All Microsoft had to do was re-skin Zune as Xbox Music and everything would have been fine. However almost all the software now is 'beta test' grade whether you use the music 'app' or pretty much anything else with Windowsphone. The cloud functionality is barely functional and it's more likely to screw up your music collection than play it. Almost nothing works. On Windowsphone the music side is a little better than the Windows 8 'app' but it just doesn't work. Every music pass owner should get 6 months refund if they have Windows 8. I would feel a little better if they had keep the Zune web streaming side of things but they closed that down.

I am thinking of radical steps to get my music service back to functional. One option is to ditch Xbox Music completely and just get Spotify now it has a Windowsphone 8 client. Another option is to ditch my Windowsphone 8 (an HTC 8x) and get a Lumia 900 from ebay so I can go back to Zune and also get videos and podcasts.

So I have a little over a month until my annual pass for Xbox Music needs renewing and it really would surprise me if the subscriber list was heading down rather than up.

Mark from CO
on Feb 22, 2013

Paul: As a user of all of your examples, you are spot on! As a WP8 user, I sometimes feel that WP8 has taken a step back in terms of functionality and ease of use (e.g. podcasts). I would include some aspects of Windows 8 in this critique as well.

Your list, and my own, would say that the majority of transitions under way fall in a category other than "good." If right, this speaks to Microsoft's lack of effectiveness in managing these transitions. At best it is far too early to say that Microsoft is no longer slow-moving and behind the times.

Prompt (rapid?) and effective execution in addressing all of the shortcomings we Microsoft users face will tell us whether Microsoft has really changed and can adapt to the new market realities. Recent events are not promising...

Jacob_Grochowski
on Feb 22, 2013

The Zune to Xbox music transition is the worst for me. Nothing just transfers over. I can't authorize my WP8 to play music files from my music pass. The desktop software is horrendous, its all just so difficult and inconvenient, but I hold on to it because I still have my Zune HD which works fine.

sekyal
on Feb 22, 2013

The XBox Music one bothers me more since Id on't use IM and a shame that MS does not seem quick to try to right their wrong (or they are unaware, which I would doubt).
But XP will undoubtedly be still used by many since those are also the people who never update their software. I assume most transitions off XP will come from the business sector. My place of work is transitioning but I wish it would happen sooner, I am so past XP, but stuck for now til they flip it for me.

Win Factor
on Feb 23, 2013

One of the things that makes me leery of MSFT is that they try things, and if they don't go well then they dump them. Part of the reason Apple is so popular is that they general haven't done big dumps (although they're getting worse - re old vs. new iPod connectors and lock-in licensing). With Microsoft:

- Plays for Sure doesn't play any more
- Windows Phone 7 was a dead end even though a quite new OS
- Windows Live is nearly dead
- Windows 8 is moving toward not having windows

Take win RT - what are the chances that this product and OS survive in 3-5 years? I'm sure some people want to buy new devices and SW every 2-3 years, but I sure don't. The >$500 you spend on your RT device could easily be an orphan. Not likely with an iPad. So people don't need to only consider the merits of the specific software and hardware, they *also* need to consider the viability of the support and the platform.

JimmyFal
on Feb 23, 2013

I didn't realize I could add messenger contacts to Lync. I never even used Lync. I forgot I had an O365 account laying around, so I'm having an aha moment replacing Skype and Messenger with Lync. When they get Skype video fused in with this, I will gladly be using this in place of Messenger and Skype. I'm going to spend the rest of today testing it out. Feel kind of dumb not having tried this before...

paulwesterman
on Feb 25, 2013

Hi Paul, why do you say 'erstwhile'? Is MS no longer a software giant? Cheers!

pthurrott
on Feb 25, 2013

Microsoft describes itself as a "devices and services" firm, not as a software maker. Even its traditional software products (Windows, Office) are now installed and serviced like online services.

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