Webmail war: Gmail vs. Outlook.com vs. Yahoo Mail

Google, Microsoft and Yahoo have all rolled out major changes to their free webmail services. Which now offers the best organization, message handling, mobile options and advanced features?

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Outlook.com

Launched in 1996 and acquired by Microsoft in 1997, Hotmail was one of the first and best-known free email services. Then Gmail ascended in popularity and Hotmail sank from view -- recently resurrected as Outlook.com, part of Microsoft's collection of Live-branded online services.

The change from Hotmail to Outlook has been, to say the least, radical. Outlook.com sports an interface patterned directly after Windows 8's UI, with lots of white space, large icons and a preview pane. The only cosmetic changes a user can make are to the color scheme used for the top bar and the fonts used for creating new messages. Also, while Gmail includes a single text-only strip of ads near the top, Outlook.com sports ads that take up the entire right-hand margin of the main window.

Outlook.com

Outlook.com sports an interface patterned directly after Windows 8's UI, with lots of white space, large icons and a preview pane.

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According to Microsoft "Outlook.com won't sell the contents of your email to advertisers, and Outlook.com keeps ads to a minimum." That said, on the page labeled "Who delivered this ad to you?", it is stated that a portion of the online ads are customized based on past online activity. The same page lets you customize the personalization or turn it off. (All the ads I was served were Bing Shopping ads for various goods and services, mostly computer-related.)

Any POP email client can be configured to download messages from Outlook.com, and the desktop version of Outlook can connect with the service via the Outlook Hotmail Connector.

One major connectivity omission for Outlook.com isn't likely to be fixed any time soon: There's no support for IMAP. Instead, Microsoft is pushing for the use of its own proprietary Exchange ActiveSync protocol. As a result, the only way to back up Outlook.com is by attaching a desktop copy of Outlook and using the Hotmail Connector.

On the other hand, you don't have to freak out about using up your inbox space: There's no storage cap for Outlook.com mail accounts.

The search functionality is pretty good. Start typing in the search box at the upper left part of the screen and you're automatically presented with a list of possible contacts, along with options to search for the term as a from:, subject: or to: query. There's also a link to an advanced search window, where you can search within a date range or by keyword, among other things. You can search by whether or not mail has an attachment, but you can't search inside attachments -- not even for content you'd think would be supported (e.g., Microsoft Office files).

That said, Microsoft Office documents emailed as attachments can be opened in Office Web Apps and are automatically uploaded into your SkyDrive account when you open them for editing. Even better, when you finish editing, the resulting document can be automatically emailed back to the recipient with a link to the in-cloud SkyDrive copy. That way you're not eating up bandwidth shuttling the file back and forth.

Outlook.com also blocks suspected viruses by way of a reputation-based system: Content from parties with a poor reputation (a hit-and-run spammer, for instance) will be blocked, but you can unblock attachments for people you trust. Some attachment types -- EXE files, for instance -- are blocked entirely, even for trusted senders.

A clutch of categories

Aside from message folders, Outlook.com comes with its own clutch of 15 pre-generated message category labels: "Bills," "Family," "Travel" and so on. You can add your own custom categories, but oddly enough you can't remove or edit the Microsoft-supplied ones. (Gmail lets you change or remove all labels.) I suspect this is at least partly because some of them use message-detection algorithms that aren't designed to be user-editable. For example, the "Shipping Updates" category pulls all messages that appear to have tracking numbers in them, which is indeed quite handy. Maybe someday we'll be able to create categories like that ourselves.

Outlook.com

Outlook.com comes with its own clutch of 15 pre-generated message category labels.

Click to view larger image

This inflexibility aside, the category system is quite useful. You can also set two different attributes for a category. "Quick view" adds that category to the list of fast-access links on the left side of the screen. "Filters" lets you take whatever folder is currently visible and apply a filter to its contents -- for instance, to see all messages from a particular person in a given folder. Messages can also be processed on arrival or on demand via a series of rules, much like the ones that can be created for the desktop edition of Outlook.

Note that if you are using a non-Outlook.com email address with Outlook.com (e.g., me@mydomain.com), any messages sent from Outlook.com through that account will be listed as something like hotmail_b9a8df14e345c8f5@live.com on behalf of me@mydomain.com. Replies go directly to the second address; attempts to reply to the remailer address will bounce.

Where Gmail lets you set up multiple mail forwarding addresses, Outlook.com lets you forward email to only one other email account at a time. Forwarded mails also have less options: The only thing you can do with forwarded emails is keep copies in your Outlook.com inbox. The setup page also notes that you should "sign in at least once every 270 days -- otherwise your account looks inactive and could be deleted."

Mobile use

Aside from Windows Phone, support for Outlook.com on mobile devices is a bit dodgy. There's no iOS app (although there is an Android one), and the mobile version of the site doesn't present itself automatically on some devices: Safari and Chrome for iPad work, but Chrome for Android brings up the desktop version of the site.

The look of the Android app also doesn't bear the slightest resemblance to Outlook.com's interface -- it's essentially a rebadged version of the old Hotmail app for Android -- but it gets the job done, and does offer contact and calendar sync with Outlook.com.

Bottom line

The revamped Outlook.com is clean-looking and works well, but the lack of IMAP support and the uncertain state of its mobile apps and mobile site is inconvenient.

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