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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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.

Yahoo Mail

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

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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

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

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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.

Copyright © 2013 IDG Communications, Inc.

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