As a Gmail user, my longstanding webmail feature request has been honest competition for Google's free service. I like being able to fire people and then spread the wealth around, but Gmail's rivals haven't matched Google's steady improvements — even as I've grown more anxious over Google's reach.
Now Microsoft is trying again with a free service called Outlook.com. Don't let the name confuse you: Outlook.com shows no relation to the dreadfully overgrown cluster of e-mail, calendar, contacts, to-do and notes tools that Microsoft reserves for $199.99-and-up versions of its Office suite.
Going by a week with Outlook.com's pre-release version — identified as "NewMail" in the screenshot above — Microsoft gives Hotmail users two major reasons to opt in and for others to sign up.
One is smarter management of the not-quite-spam messages — sometimes called "graymail" or "bacn" — that you sign up for but don't necessarily value: daily-deals offers, retailer newsletters, shipping notices, social-network updates and so on.
Outlook.com tries to categorize these messages automatically, then lets you dump those older than a set interval with a "Schedule Cleanup" command. An "Unsubscribe" item in its Actions menu can then free you from scanning the fine print of an e-mail (except when, as in the case of a Home Depot mailing, Outlook didn't display that shortcut).
This new mail service can also display a contact's Twitter, Facebook and LinkedIn profiles in a sidebar, should you give Outlook access to those accounts. This provides valuable context about what people have said elsewhere, but you may need to link their e-mails with Facebook or Twitter accounts first; Outlook.com got fooled when a friend's work address listed his last name first.
And there are no ads keyed to the content of your messages. That makes me want to like this service.
But Outlook.com falls short of Gmail in aspects that matter to me, if maybe not you. Using a custom domain name is harder than at Google (one reason I host my work e-mail there); you can staple on a different "from:" address, but that can leave recipients seeing a "via" or "by way of" suffix showing the Outlook.com address.
And offline synchronization to computers and phones suffers from Microsoft's choice of a proprietary system. Where Google employs a standard called IMAP that lets you use pretty much any e-mail client around, Outlook.com requires not just Microsoft's Exchange ActiveSync but one flavor of it.
So while you can use Microsoft's Outlook for Windows, Windows Live Mail and Win 8's underdeveloped Mail, Mac users can't leave their browsers. Neither Microsoft's older Entourage or its current Outlook for Mac sync with Outlook.com. Apple's own Mail for OS X can't either–even though its iOS version does.
This easily beats Yahoo's sadly-neglected webmail. But if I want to upgrade my work account from Gmail, it still looks like I'd have to pay for the privilege.
Credit: Rob Pegoraro/Discovery