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Managing Your Life in the Clouds: A Guide for Windows Users, Part 1: The Microsoft Experience

My recent foray into Apple's disastrous MobileMe service (see my perhaps overly-lengthy review) got me thinking: Sure, MobileMe is a car crash of historic proportions. But it's a good idea. Is there anything else out there that rivals what Apple's service promises or at least delivers? And what's the prognosis for cloud-based services from online heavyweights like Google, Yahoo!, and, yes, Microsoft? Do they offer a viable alternative to MobileMess?

As it turns out, yes and no. I don't like to waffle when it comes to rating products and services, but let's be honest for a moment. As I write this in the waning days of summer 2008 (at least here in North America), no one service does it all. I'm talking excellent email and contacts management that works well on the Web, in native Windows applications, and on the go, with an iPhone or other mobile device. A standards-compliant calendar with the same level of access. Photo management. Online storage. All the good stuff Apple promises but doesn't quite deliver with MobileMe.

Granted, we're in a transitionary period now. And if MobileMe has just one positive effect on the industry, it will surely be this: It will inspire Apple's competitors to get their acts together and deliver a pervasive cloud computing experience that works where we want it to work, whenever we want it to. For now, well, not so much. And you thought MobileMe was a mess.

First up: Microsoft.

The Microsoft approach

Of the three heavyweights here, Microsoft, perhaps, has the best approach. It certainly has the broadest, most well-rounded offerings. Here's how it plays out:

Web solutions

Though Microsoft is most famous for its desktop computing solutions, the company has amassed a surprisingly deep set of online offerings as well.

Email: Windows Live Hotmail (,,

Contacts: Windows Live Contacts

Calendar: Windows Live Calendar (beta)

Photo management and sharing: Windows Live Spaces (blogging solution); MSN Soapbox for videos

Online storage: Windows Live SkyDrive, Office Live Workspace, Live Mesh

Notes: All of the online services listed here are free. However, customers can purchase a Hotmail Plus account for $20 a year to get additional storage space. Hotmail is enormously popular and Microsoft's 2007 revamping of the service has been hugely successful, sporting a true Web 2.0 interface with right-click and drag and drop support, akin to a desktop application. Performance is average, however, and you can't use a custom domain name for Hotmail-based email. (Update: This is incorrect. Check out Microsoft's Windows Live Domains for more info.) WL Contacts is an excellent contacts management system and it also integrates with Windows Live Messenger, Microsoft's instant messaging (IM) platform. Windows Live Calendar is, perhaps, the weakest link in the chain, given its beta status and incomplete feature-set. Windows Live Spaces is acceptable as a standalone photo management and sharing solution, if your intention is to share photos in a blog-like fashion. But you have to host your site on; Microsoft does not provide a way to move your space to a custom domain or, for that matter, to buy extra storage. Windows Live SkyDrive is arguably the best online data storage solution for consumers right now, but it's limited to 5 GB of storage space and as with Spaces, there is no way to purchase additional storage. Office Live Workspace is a document collaboration solution that's build on the SkyDrive platform. Live Mesh is a burgeoning cloud computing platform; in its current pre-release state, it offers PC-to-PC-to-cloud file synchronization (with 5 GB of cloud storage, but unlimited capabilities on the client) and remote desktop functionality.

Verdict: Microsoft's Web-based solutions are good to excellent across the board. Live Mesh is particularly compelling, though it offers no services that are specific to this topic.

Desktop solutions

Not surprisingly, Microsoft's desktop software products typically offer tight integration with the company's online services. This is particularly true of email/contacts and photo management.

Email: Windows Mail (Windows Vista; free), Outlook Express (Windows XP; free), Windows Live Mail (free), Outlook 2007 (~$100, or part of many versions of Microsoft Office).

Contacts: Windows Contacts (Vista), Windows Address Book (XP), Outlook 2007

Calendar: Windows Calendar (Vista), Outlook 2007

Photo management and sharing: Windows Photo Gallery (Vista), Windows Live Photo Gallery (XP and Vista; free)

Notes: Microsoft's email applications range from average (Outlook Express, Windows Mail) to spectacular (Windows Live Mail, Outlook). Note, however, that the company's Hotmail service will not work with any non-Microsoft email applications at all, so you literally have to access this service via the Web or a Microsoft application. All of Microsoft's email applications work with any POP or IMAP account; Outlook supports Exchange as well. Windows Live Contacts integrates directly with Windows Live Mail and Outlook (using the free Outlook Connector), but not with Windows Address Book or Windows Contacts (for which you'll need to perform a manual import/export). Windows Live Calendar integrates only with Outlook (using the free Outlook Connector) at this time, limiting your choices. Microsoft's Windows Live Photo Gallery application is first-class, and integrates nicely with Windows Live Spaces (photos), MSN Soapbox (videos), and even Yahoo!'s Flickr (photos). Microsoft doesn't offer any direct client support for Windows Live SkyDrive, which is odd. So you're forced to use the Web interface, which works better in Internet Explorer than it does in rival browsers. However, Office Live Workspace users can take advantage of integration functionality with Office 2003 and 2007, letting them save and open documents in the cloud using familiar desktop tools.

Verdict: Microsoft's desktop solutions are largely excellent and offer tremendous integration with the company's online services.

Mobile solutions

Microsoft creates the Windows Mobile operating system for smart phones, but it also creates limited versions of its Windows Live services for certain Blackberry and Nokia phones. I'll focus on Windows Mobile here, since it offers the most comprehensive functionality and is a core part of Microsoft's strategy. The latest version of Windows Mobile, 6.1, is only available currently in a handful of phones.

Email: Outlook Mobile provides email sync with Outlook, OTA push support for Exchange, and native support for Windows Live Hotmail email.

Contacts: The Windows Mobile Contacts application syncs with Outlook on the PC, and with Exchange Server. Using Windows Live for Windows Mobile, Contacts also syncs with Windows Live Contacts. All contacts are presented in an aggregated view on the device.

Calendar: The Windows Mobile Calendar application syncs with Outlook on the PC, and with Exchange Server. Notably, Windows Mobile Calendar also supports Outlook Tasks.

Photo management and sharing: Windows Live Spaces for Mobile provides photo uploading from the phone and blogging capabilities. Windows Mobile devices include a basic Pictures & Videos application for managing photos on the device.

Notes: Users who buy into the wider Microsoft ecosystem will get a pretty seamless experience if they use a Windows Mobile device. Despite the relative weaknesses of the underlying platform, Microsoft provides mobile versions of Excel, Word, and PowerPoint, as well as Outlook Mobile E-mail, Contacts, and Calendar. Internet Explorer Mobile (previously Pocket IE) offers rudimentary Web browsing capabilities. Windows Live for mobile is a comprehensive mobile suite featuring deep integration with Microsoft's online services, including unrelated products like Live Search, Messenger, and an excel Local Search. MSN Mobile provides a mobile entertainment, news, and weather portal.

All that said, for the best Windows Mobile experience you will need Outlook: Windows Live Mail, Windows Calendar, and Windows Contacts are not directly supported. Still, Windows Live users can access their email and contacts on Windows Mobile devices directly, somewhat offsetting this issue. (This isn't true of Windows Live Calendar, which is currently in beta.)

Verdict: Microsoft's mobile platform needs a lot of work, but if integration with the company's online services and desktop products is the goal, and you're an Outlook user, Windows Mobile is the way to go.

Final thoughts

At the time of this writing, Microsoft offers a comprehensive but incomplete cloud computing experience that provides Web-, desktop-, and mobile-based access to most of its offerings. In this sense, Microsoft's PC history has paid off, with the company seizing on mobile and Internet opportunities as they arose and embracing and extending their core experiences, as it were. What really separates the Microsoft experience from the Google and Yahoo! experience of 2008 is that you won't typically have to do any manual patching together of your own if you stick with Microsoft, as the software giant ensures that everything it does--for the most part--works on all of its relevant platforms.

In other words, if you go the Microsoft route, you can access your Hotmail email from the Web, from any number of (Microsoft only) desktop applications, or via a native application on your Windows Mobile device. (And, perhaps, via certain Blackberry and Nokia devices. Otherwise, you're stuck with the lackluster mobile Web version.) Ditto for contacts: Your Windows Live Contacts can be synced to the desktop with Outlook (and the Outlook Connector) or Windows Live Mail, and to a Windows Mobile device using the device's native Contacts application. Calendar is currently the weak point, but Windows Live Calendar is still in beta and should be straightened out by the end of the year.

Speaking of weak points, other areas of concern with the Microsoft experience include Windows Mobile, which is notably rough compared to Apple's iPhone, and the lack of support for native Vista applications like Windows Calendar and Contacts.

Still, the overall Microsoft cloud computing experience is very good. And that's pretty impressive when you consider that, of the three companies being surveyed here, Microsoft is the only one that doesn't have cloud computing in its DNA: Both Google and Yahoo! were created as Internet companies.

Next: The Google experience ...

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