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

Which now offers the best organization, message handling, mobile options and advanced features?

By Serdar Yegulalp, Computerworld |  Unified Communications, Yahoo, email

There's little question that Web-based email has captured a major portion of the user base. The conveniences of webmail -- all your messages in one place, few or no practical limits on storage, access from almost any client device -- make it all the more appealing to generations of users for whom client apps like Outlook are clunky relics.

Trouble is, hard numbers can be tough to come by. Google, for instance, claims that as of June 2012 Gmail alone had some 425 million users, although analytics firm ComScore gave an estimate of 289 million for May 2012. The other two major contenders -- Yahoo Mail and Hotmail (now Outlook.com) -- were in about the same ballpark, according to ComScore, with 298 million and 325 million users, respectively.

The picture is further complicated by other issues, such as how many users have accounts on more than one service, how many accounts are abandoned, how reporting on mobile versus desktop is skewed, and so on.

Fuzzy as the hard numbers might be, any service type with a user base in the hundreds of millions is worth keeping fresh. Over the past year, each of the three largest webmail providers has made major changes to its service.

In the case of Gmail, those changes have been part of the rolling tweaks Google makes throughout its family of services. On the other hand, Microsoft has pushed through a major rebrand and relaunch, turning its well-known Hotmail email service into Outlook.com, with an entirely new interface and overhauled feature set. Yahoo has also been attempting to reinvent itself, giving its service a new look and some new features.

In this roundup, I look at what's changed for each email service during the past year -- both cosmetically and functionally -- and the ways each implements commonly used features: mail organization and searching, POP/IMAP access, handling of attachments and the mobile experience (including apps).

(Story continues on next page.)

How to switch email accounts

One of the biggest problems with using a webmail account is leaving it and/or going to another. None of the accounts profiled in this piece have an obvious way to export your email and your contacts, and move them to another service. That doesn't make it impossible, though.

Moving email

Gmail lets you import email from another provider; you can also have messages forwarded from the provider to your Gmail account for up to 30 days. Most popular mail services are supported, and I was even able to set up a link from my own vanity email address after manually specifying the needed POP3 login information. If your provider isn't one of those that Gmail imports from, Google has a tool it calls the Mail Fetcher, which lets you download messages from up to five accounts.

Leaving Gmail is trickier. Third-party services, such as the command-line Got Your Back and Gmail Keeper tools, or online apps like Backupify and BackupGoo, can be used to automate the process without needing much babysitting.

With both Gmail and Yahoo, the easiest way to export your email is via IMAP connectivity, which is supported by each service. Install an email client that supports IMAP -- such as Outlook or Mozilla Thunderbird -- then download your email locally.

You can also import email to Yahoo using this method, but it's not easy. When you set up a local mail client for IMAP, you can copy mail to or from the remote IMAP folders. So if you have two services set up in the same mail client via IMAP, you can transfer mail between them simply by copying them between remote IMAP folders.

The process is slow and a bit tedious, especially if you have a lot of folders, but it can be done. And this, or using a third-party application such as TrueSwitch (see below) is the only way to import email to Yahoo.

Outlook.com does not support IMAP, but you can use Microsoft's Outlook Connector tool, together with Outlook (the desktop application, which does support IMAP), to accomplish the same thing. (The Outlook Connector is built into Outlook 2013 and Outlook for Mac 2011; it can be installed to earlier versions.)

While there is no built-in import mechanism for Outlook.com, there is at least one third-party outfit that might help. TrueSwitch copies email messages and contacts from one account to another for you, provides mail forwarding between accounts, and notifies contacts of the upcoming change in address. TrueSwitch is free for some services, such as Gmail and Outlook.com; it will also work with Yahoo, but you have to purchase a copy of the software for $29.95.

Moving contacts

Migrating contact information, thankfully, isn't as hard. Gmail (and Google generally) makes it easy to do this. The Google Takeout service lets you create an archive which contains data associated with your various Google accounts. Contacts information can be downloaded as a CSV file, vCards or as an HTML file.

If you're migrating to Gmail, importing contacts can be done via CSV or vCard. Google has documentation for how to import CSV files and how to format them for use in Gmail.

One very nice feature of Yahoo's contact export option is the variety of formats. Not only does it export in Outlook-friendly CSV files, but also a CSV format recognized by Yahoo itself (in case you want to re-import to a new account), a Mozilla Thunderbird-native format, and either multiple vCards in a ZIP file or a single vCard. Contacts can also be imported from a whole plethora of sources -- another Yahoo account (you'll need the login and password), a variety of social networks or as a CSV file exported from a desktop program.

Importing contacts into Outlook.com isn't hard; it can be done via a CSV file exported from Outlook or another program. Exporting is also simple; just go to the "Export" option in the "People" submenu, click that and you can download a CSV copy of your contacts. The bad news is that this copy, at least as of this writing, doesn't include contacts imported from social networks (Facebook, Google+, Twitter); it's only contacts that you have added directly in Outlook.com yourself or imported via a file.

Gmail

Gmail currently provides email for an estimated half a billion users, according to its own internal stats, with at least 10GB of email storage for every one of them. In the last couple of years, Gmail has shed its "perpetual beta" stigma -- something that was common to many Google applications -- and has become a service that, it sometimes seems, just about everyone has an account with.

Google's Gmail recently underwent a redesign, and elements are now spaced wider apart.Click to view larger image

The most visible of Gmail's changes in the last year or so, apart from placing Gmail under the recently unified Terms of Service that were rolled out across Google, involves a redesign of its interface. Elements are now spaced wider apart, an echo of the visual changes made across Google systemwide. If you'd rather stick with the previous look, Google has provided a way to change back: Click the gear button on the right side of the main screen and select "Compact" from the list of possible views to restore the old, more closely spaced view. You can also customize the look and feel with various themes (in contrast to Outlook.com, which allows only basic customizations). One thing still missing from the interface (and provided by both Yahoo Mail and Outlook.com) is a message preview pane option.

Gmail differs from most other email services in the way that it handles message replies. With Google, the standard reply is edited via a frame nested at the bottom of the original message (as opposed to Outlook.com and Yahoo Mail, which open a new tab or window). This is handy if you want to keep both the original message and the reply in front of you as you edit. You can also pop out the reply into its own subwindow and edit it separately -- and since I tend to work on multiple mail drafts at once, this is a welcome feature for me.

Gmail is closely integrated with the rest of the Google ecosystem in a variety of ways. If you use the Google+ social network, for example, messages from that service are indicated in your inbox via a "g+" icon next to the subject line. Hover over the name of a sender and contact information appears, along with any Google+ circle membership you have for them. If you use Google's Chrome browser, Gmail can be used as the default email handler. And a feature currently in field trials allows you to see search results from your email when searching Google generally.

Gmail, like Google's other free-to-use services, is ad-supported. Ads are contextual and personalized -- they're served based on what sorts of emails you've been receiving -- but you can opt out of personalized ad delivery if you wish.

Another major set of changes involves support for new mail-related protocols. Gmail has long supported IMAP and CalDav, but a new addition to the mix includes CardDav, for contact management with third-party clients like Thunderbird or the contact manager in iOS.

On the downside, Google recently discontinued the consumer version of Google Sync for Microsoft Outlook, which allowed Outlook users to keep their calendars, mail and contacts in sync with Gmail. Those who want to continue syncing have two choices: Pay for a Google Apps for Businesses account, which supports sync, or switch to an email client that supports CalDav and CardDav (e.g., Mozilla Thunderbird). Other Google Apps account features include the ability to use a custom (non-Gmail.com) address, a bigger inbox, uptime guarantees and live support.

In Gmail, the standard reply is edited via a form nested at the bottom of the original message.Click to view larger image

If you use IMAP to access Gmail from more than one device, take note of the "recent mode" feature. This allows the last 30 days' worth of mail to be made available to multiple devices, whether or not it's already been downloaded -- handy if you want to keep offline copies of mail on more than one device. Another nice touch for IMAP users: All folders, apart from the Inbox, can be optionally hidden from IMAP clients to streamline the download process.

Organizing with labels

On top of its usual type-to-search functionality (which returns results from your mailbox, your Google+ circles and your contacts), Gmail has an organizational system that lets you create hierarchical lists of labels (it uses the term "labels" rather than "folders") that can be applied to email. Apart from the usual Inbox, Trash, Drafts, Archive, etc., you can also create your own labels. The labels are all listed on the left side of the window; click on a label to see only messages with that label.

Within each label category, you can star individual messages (and then see just those by clicking on the "Starred" label). Google also lets you indicate which messages you consider important by clicking on a small flag-like icon in your message list. Over time Gmail will figure out what messages you consider important and automatically flag them; you can then see all such mail in a special view (labeled, appropriately, Important). If you want all your important, starred and unread email to be on top of your list, you can choose Priority Inbox.

Attachments in messages can be downloaded singly, en masse, or -- depending on the file format -- viewed either in-browser or through Google Docs. I had trouble getting some larger, more complex Word documents to render in the latter, but files like PDFs and images worked fine. Gmail also scans attachments for viruses and will bounce incoming messages or block attachments, incoming or outgoing, that appear to be infected.

I was disappointed that it isn't possible to export an archive of your email via the Google Takeout data-portability service, but (as detailed in our sidebar) you can use an independent email client such as Mozilla Thunderbird to accomplish the same thing via its native IMAP connectivity. I tried this once, and depending on how much email you have, it can take many hours.

Auto-forwarding from Gmail can be done by simply adding one or more forwarding addresses via your account settings. The addresses you list are confirmed by sending a confirmation code to the address in question. You can also opt to have forwarded mail kept intact in Gmail, marked as read, archived or deleted entirely.

Mobile use

For mobile devices, Google makes dedicated apps not only for Android but for iOS as well. The new 2.0 version of the iOS edition lets you access multiple Gmail accounts, works directly with various Google service requests (e.g., if you get a calendar invite, it's handled right in the app), and lets you post to Google+ through email.

Users of the Chrome desktop browser can add Gmail Offline, which caches up to a month of mail directly in your browser for offline access via the magic of HTML5, although it makes the layout and format of Gmail look a lot closer to the iOS app than to the desktop website.

And the mobile-site version of Gmail is also very nicely designed, with a remarkable amount of easy-to-access functionality crammed into a small space.

Bottom line

Google's Gmail email service is still a fine choice, rich with meta-organizational features and external connectivity options -- although its highly useful sync features for Outlook are now only available for paying customers.

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 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.

Read more about web apps in Computerworld's Web Apps Topic Center.

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