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

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 sports an interface patterned directly after Windows 8's UI, with lots of white space, large icons and a preview pane.Click to view larger image

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 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.

Yahoo Mail

Yahoo's email service got a major revamp at the end of 2012, one of the major changes ushered in since Marissa Mayer's entry as CEO. The new Yahoo Mail is uncluttered and clean but lacks many of the advanced management and categorization features of its competitors -- unless you pay for them.

That's the catch: The free tier of Yahoo Mail is deliberately crippled in certain ways. For $19.99 a year, Mail Plus disables ads, allows you to use POP and set up mail forwarding, lets you use up to 200 filters (the free version lets you use up to 100) and doesn't require you to log in every so often to keep your account from being shut down. My favorite paid feature: Disposable Addresses, which lets you create proxy addresses you can use without having to give away your actual address.

The new Yahoo Mail is uncluttered and clean but lacks many of the advanced management and categorization features of its competitors.Click to view larger image

If you prefer to use the free version, then (like most free webmail), Yahoo Mail is ad-supported. The AdChoices ads on the right side of the page are served via flash, making them easy to block if you wish -- either by blacklisting flash for the mail.yahoo.com domain in your browser or by disabling flash, in which case the ads drop back to static images.

I did like the option for a preview pane when reading email, which made the experience a bit more like working with a full-blown desktop client. The only other customization options are sets of color themes, and the spacing between lines on the display (the latter akin to a feature Gmail offers).

I also liked the way opened emails and search results are placed in their own tabs within the Yahoo Mail window so they can be kept open and referred back to if needed. Unfortunately, those tabs don't persist if you close and reopen Yahoo Mail, and you can't retain tabs for several searches at once except by performing the searches in entirely different browser windows.

While Yahoo does support IMAP connections, they're supposed to be used only on mobile devices and not desktops, although there's no practical way to prevent people from using the connections as they want to. POP is supported only if you buy Mail Plus, although third parties like YPOPs have created proxy systems to allow POP access. Likewise, no direct way exists to back up or migrate email out of Yahoo, save for using IMAP or a third-party product like MailStore Home.

There's a box at the top of the main mail window for searching either your email or the whole Web, the latter courtesy of Bing. The resulting searches can be narrowed by various criteria -- sender, date, folder, etc. Interestingly, the contents of certain types of email attachments do seem to be indexed for search. (I got results from my PDFs and my legacy Word DOC files, but not the more recent Word DOCX files.)

Email attachments are scanned by Symantec's Norton AntiVirus before being downloaded, and recognized image file types (JPG, GIF) can be shown inline as a thumbnail before being downloaded. Email messages forwarded as attachments will also have the text of the attached message show up inline, which saves you the trouble of unpacking the attachment. Another nice touch: If someone emails you a whole pile of files, you can click "Save All to Computer" to download them all in one go.

Yahoo Mail allows you to add apps, essentially plugins for your mailbox, which are provided by third parties though Yahoo.Click to view larger image

Yahoo Mail allows you to add apps, essentially plugins for your mailbox, which are provided by third parties though Yahoo. Some of Yahoo's own services have apps as well -- for example, Flickr, which lets you share photos easily from your Flickr account. I also liked the Attach Large Files app, courtesy of YouSendIt (which I reviewed not long ago), a way to send big files to someone else without choking their inbox. The number of apps right now is small -- only 10 or so -- but that may just be because the revamped Yahoo Mail is still such a new product.

Limited organizing

Yahoo Mail's biggest drawback is its almost complete lack of organizational tools. You can create folders, but they can't be arranged in hierarchies. The only other way to organize messages is by starring them as important, but apart from that there's no way to tag or otherwise apply metadata to mail.

Yahoo Mail does offer a system for filtering incoming mail via matching keywords against the header or body of the message. In addition, the menu for any given email message includes a "Filter mail like this" option to pre-populate a filter with the selected message's attributes.

You can only automatically forward email to another account in the for-pay version of Yahoo Mail, and you can only forward to one email address at a time. You can retain forwarded mails in your Yahoo inbox if you need to.

Mobile use

Yahoo hasn't skimped on providing mobile apps for Mail. Clients exist for iOS (optimized for the iPhone) and Android. In addition, its mobile site is fairly polished, adjusting the layout of its display based on the size and type of the accessing device.

Bottom line

Yahoo Mail is easy to work with and approachable, but all the features that would make it even more useful are either behind a paywall or absent entirely.

Conclusions

For those who haven't considered Hotmail since Gmail came along, Outlook.com is a welcome surprise, even if there's no support for IMAP and its mobile experience could still use some work. It's going to be one to watch, especially with Microsoft's growing push toward being a services outfit for end-users instead of just all-Windows, all the time. Meanwhile, Yahoo Mail is a decent entry-level product for undemanding users, but it's easy to see people outgrowing it quickly.

Folks who are uncomfortable with the way Gmail offers up ads based on the content of email (however automatic the process) might want one of the other services. Another big gripe I have with Gmail is how a key piece of its functionality -- client sync -- has been shunted out of the free product and into the for-pay tier. I hope this isn't a trend.

But in the end, it's hard to go wrong with Gmail. It's been broadly adopted, has a solid feature set and supports most of the popular mail protocols.

Serdar Yegulalp has been writing about computers and information technology for over 15 years for a variety of publications.

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