Gmail vs. Outlook.com: Which offers the best email in the cloud?

POP/IMAP support

Any good webmail service should be able to send and receive mail from other accounts, thus allowing you to manage multiple email addresses (including work and personal accounts) under one roof. Gmail earns high marks in this area, offering support for both POP and IMAP. But Outlook.com supports only POP, so synchronizing mail accounts among multiple mail clients is much tougher. For example, the mail you read on your laptop won’t sync with the mail you read on your smartphone, and vice versa. (The exception is if you connect via Microsoft’s Exchange ActiveSync; see “Mobile access” below.)

Prefer IMAP? You're out of luck with Outlook.

That’s a potential deal-breaker for some users, and arguably it's the only area where Outlook.com has a fundamental shortcoming compared with Gmail. For the former to compete, Microsoft needs to add IMAP support, stat.

WINNER: Gmail

Gmail caps attachments at 25MB.

Attachment handling and storage

When you receive a message containing, say, a Word file or PowerPoint presentation, opening that attachment should be a simple matter. Thankfully, both Gmail and Outlook make the task pretty darn simple.

I emailed a Word document to both my accounts. Outlook made a prominent show of the attachment, complete with a familiar-looking Word icon atop the body of the email. One click, and the document downloaded immediately in its native format (ready for viewing in Word proper), though I also had the choice of downloading it as a .zip file. Or, by clicking View online, I could view the document in Microsoft’s Word Web App, with the option of making quick edits right in my browser.

Gmail operated similarly, with simple View and Download options; the former steered me to a Google Docs viewer and, if I wanted, a full-blown editor.

Outlook lets you attach a 100MB file (and even larger items with a hand from SkyDrive).

As for attachment size, Gmail limits you to files no larger than 25MB, while Outlook.com caps them at 100MB—or 300MB if you establish a link to your SkyDrive account. And speaking of storage, Gmail gives you just 10GB, while Microsoft promises an unlimited inbox. Granted, expanding your Gmail storage space doesn’t cost much, but why pay if you don’t have to?

WINNER: Outlook.com

Mobile access

For now, the option to add Outlook.com to your iPhone isn't obvious.

Want to access your Gmail or Outlook.com account on your smartphone or tablet? With Gmail it’s a snap; Android devices have the service built into their DNA, and iOS devices list it prominently when you go to add a mail account.

With Outlook.com, things are a little trickier. iOS still has a button for Hotmail, not Outlook.com, on the list of compatible mail services. You can still use it to sign in to your account, but if you have a different top-level email address associated with your Microsoft account, that’s what will appear when you try to compose a new message.

The better option is to set up Outlook.com via Microsoft Exchange—or “Corporate” if you’re on Android. Setup can be a hassle, though, and Microsoft doesn’t make it easy to find the proper domain- and server-setup instructions. The good news is that once your account is configured, you’ll get IMAP-style syncing.

WINNER: Gmail

The overall winner

As with classic prizefights such as Mac versus PC and Coke versus Pepsi, we have no clear-cut winner; in the end, your choice may merely depend on which features and capabilities you prize the most.

Both Gmail and Outlook.com let you manage work and personal identities with relative ease, funneling various accounts and assigning them their own folders. However, it’s important to note that because Outlook.com doesn’t support IMAP, you may have a harder time working with corporate accounts.

For those keeping score, it’s Gmail by a nose. (See the chart below for more side-by-side comparisons.) But give credit to Outlook.com for being a close second, and for offering a more visually pleasing and intuitive email experience. Can you get your work done using Microsoft’s new service? Absolutely, especially if you deal with a lot of attachments and plan to store massive amounts of email.

On the flipside, Outlook.com could pose a problem for small businesses that need IMAP support and don’t have the tech expertise to deal with Exchange ActiveSync. What’s more, while Gmail can take your inbox to new places thanks to add-ons such as Boomerang for Gmail and SmartrInbox for Gmail, Outlook.com has no add-ons—at least for the moment. It's no surprise that the desktop Outlook and its corporate, cloud counterpart (Outlook Web Access) offer richer features than the fledgling Outlook.com does.

Gmail vs. Outlook.com

FEATUREGmailOutlook.com
Users 425 million, with 4 million for Google Apps for Business 360 million for Hotmail, 10 million for desktop Outlook
Interface Stark and cluttered, with no preview pane and a confusing side panel Clean and inviting, with a choice of right or bottom reading panes and a nice use of fonts
Security/privacy Two-step authentication One-step authentication
Ads Personalized ads based on the content of your email; no opt-out Personalized ads based on your browsing history; you can opt for generic ads instead
Email organization Labels, filters, priority inbox, optional conversation view Folders, categories, Quick Views, optional conversation view
Mobile Natively supported on all major platforms Works with major platforms, but some manual configuration may be required
Storage 10GB Unlimited
Spam filtering Yes Yes
Chat Built in Built in
Paid editions Stepping up to Google Apps allows for custom email addresses and more storage Not applicable
Integration with productivity tools Google Apps/Drive suite Word, Excel, and PowerPoint Web apps; SkyDrive
Contacts Google Contacts People
IMAP support Yes No

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