Business

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

Search

Even if you’re diligent about deleting old or unnecessary email, it’s a good bet that your inbox contains hundreds—if not thousands or even tens of thousands—of messages. So how can you possibly hope to find a single email needle in the haystack that is your inbox? With a robust search engine, of course.

Outlook.com covers the basics fairly well. You can type a keyword into the search field, or click Advanced and add the sender, subject, folders, and/or dates to the mix. Nothing fancy, but it works.

Outlook's search is functional, not fancy.

Of course, as you might expect from a Google product, Gmail buries the competition. You get dynamic search parameters that appear as you type in the search field. You can refine your search any number of ways, adding operators for items such as attachments, labels, and even Google+ circles. Best of all, Gmail lets you turn any search into a filter, thus making it simple to run again in the future.

WINNER: Gmail

Mail organization

It’s not uncommon to use your inbox as a filing cabinet, a storage facility for important messages from coworkers, customers, and other business contacts. But Gmail and Outlook.com take decidedly different approaches to organizing all those messages.

Outlook.com's Quick Views are unique.

Outlook.com relies on a traditional folder system, allowing you to create as many folders as you like and to arrange them hierarchically by dragging and dropping. Likewise, you can drag email messages into those folders. But Outlook also lets you assign messages to categories, which you can then use for Quick Views—filtered lists of messages that make it simple to find mail of a specific type, such as newsletters, notes from the boss, or mail with attachments.

Gmail has long championed its system of labels and filters over folders, and although that system has its merits, some users have a hard time wrapping their brains around it. The arrangement is less intuitive and less familiar. However, Gmail’s superlative search capabilities help to mitigate any such obstacles: Why bother organizing at all when you can so easily search for what you need?

It’s hard, then, to answer the question of which system is better. Ultimately the answer depends on what you’re used to and how you like to organize. Both systems are effective; they’re just radically different.

WINNER: Tie

If you're interested in POP and IMAP options, Gmail supports both.

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