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Microsoft’s Email Musical Chairs

A large tech company has to offer a free email service to be relevant these days, I suppose, particularly if they delve in search. Build a pretty site, add lots of features, and offer the accounts free. Sure, there will be targeted ads polluting the site to generate some revenue for the company, but I suppose most of you have come to accept that. Well, at least if you get your Hotmail/Live Mail, Gmail, or Yahoo! email online.

I haven’t included Apple’s former MobileMe service in the mix, since it’s no longer available, although those mac.com and me.com addresses — soon to be supplemented with icloud.com — are still working under iCloud. But free email is not the major part of iCloud, and Apple doesn’t inflict advertising on you.

Now Microsoft’s original email service, Hotmail, was dogged with a nasty reputation as a spam magnet. The reputation was well deserved at first, but, to its credit, Microsoft has doubled down on improving spam protection. But the same is also true for Yahoo! and Gmail.

Microsoft, however, has a penchant for renaming under-performing services in the hopes that rebranding and a little interface refinement will add up to more users. So Live search become Bing, with mixed results. Microsoft took an over $6 billion write-down in the last quarter because the online advertising agency they bought to compete with Google failed to deliver the goods. Bing has simply cannibalized more market share from Yahoo!, which uses the Bing search engine. Google continues to control two-thirds of the search market.

This week, Hotmail became Outlook. Certainly the name Outlook has a good reputation, since it’s the name of business email clients for the Mac and PC, so you are presented with the veneer of an industrial grade service with a neat, if cluttered, look and feel. The rebranding also means that, if you hurry, you can get an outlook.com email alias to match the one you used for hotmail.com or live.com. Yes, I grabbed my name, and spent a while navigating the new service to see if it is at all worthwhile.

Outlook has one leg up on Gmail, because the latter remains crowded and geeky. There are loads of features, some of which are barely understandable, some of which are still in beta. Some of you are still confused by Gmail’s peculiar setup, which uses labels instead of folders. If that seems a distinction without a difference, it basically means that the message isn’t technically being moved anywhere. It just gets a different label applied to separate it from other messages for easier organization. There’s also an All Mail category that puts everything in one place, and that can also be a major source of confusion.

Despite the oddities, Gmail remains extremely popular. According to a November 2011 Comscore report, the service had 260 million users, but Google reported 425 million Gmail users as of June of this year, perhaps because of the popularity of the Android Mobile platform. Last year’s Comscore survey pegged Hotmail, then, as the most popular free email service, with 350 million users, followed by Yahoo!, with 310 million.

Armed with those stats, I can see where Microsoft, feeling it had indeed fallen behind the curve, decided to rebrand Hotmail as Outlook, in hopes that the service would be taken more seriously.

When you compare the three, you’ll find they all appear to deliver pretty credible service, and spam protection is really quite good. User settings for Outlook and Yahoo! are fairly basic, with similar features. You can, for example, create new message folders, filter email, or retrieve messages from other services.

But if you want to forward email from one of these services to another account, you’ll find that Yahoo! puts up a roadblock. You’ll need to upgrade to Yahoo! Mail Plus, at $19.99 for the year. This premium service removes the targeted ads, and also gives you forwarding capabilities, and the ability to “POP-out,” which means accessing your Yahoo! from a regular email client, such as Apple Mail and, for that matter, Microsoft Outlook for the Mac and Windows.

However, there is one area where Outlook and Yahoo! mail fall down on the job, and that’s providing support for IMAP email. Now I’ve long recommended IMAP as the best way to set up your account on a regular email client. With IMAP, messages are stored on the server, meaning that you can retrieve the same messages on any desktop or mobile computer and know everything will be in sync. The Sent messages in Apple Mail will also find themselves in the Sent folders on an iPhone, or even an Android phone.

It’s true the setup for IMAP isn’t quite seamless. You usually have to manually map the email client’s standard local folders (Sent,  Drafts, Junk and Trash) to the corresponding ones on the server. Desktop email clients seldom do those setups automatically, which adds one level of confusion to the usual account setup process. In passing, I find that Mail for the iOS tends to get these settings correct without much manual intervention.

Among the top three free email services, only Gmail supports IMAP. Curiously, of all the reviews of Outlook that I’ve read so far — and most praise it to the skies — the lack of IMAP support isn’t being mentioned. These reviewers must assume you’ll only retrieve Outlook email from a browser, and that full support for regular email clients doesn’t make a difference. But it does.

The lack of IMAP support means that, while I will keep my outlook.com email address, I’m not going to use it very often. Microsoft probably doesn’t realize why that feature is missing, or what they have to do to add it to the service. But the same is true for Yahoo!

And, yes, Apple’s free iCloud email does support IMAP, and the online interface is simple and snappy, reminiscent of Apple Mail on your Mac. As for Outlook, Microsoft should be proud they signed up one million users in the first 24 hours, which is less than the number of people who downloaded OS X Mountain Lion during the same period.