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.
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