Microsoft's Hotmail e-mail gets a makeover

Hotmail looks better, works faster and adds some neat features. Can it compete with Gmail?

According to Microsoft, Hotmail is the world's largest Web-based e-mail service, with more than 360 million active accounts worldwide. But when it comes to buzz, Gmail has had it beat for the past several years. Now that may change. A revamped Hotmail was announced on May 18; it will be available sometime in July or August, with the exact date still to be determined.

I was able to work with the new version and found that it has the fast responsiveness and full feature set of a desktop application rather than a Web-based one. It also offers some very nifty features that Gmail is lacking, including better mail management and more ways to eliminate e-mail clutter.

Better interface

To begin with, the new Hotmail simply looks better -- it's more graphical and easier on the eyes. And it feels faster and more responsive. Like the old Hotmail, folders are on the left-hand side of the screen, and the in-box and reading pane on the right. But that basic layout has gotten a makeover, with a number of links added to the left side of the screen and a new set of links across the top of the right side of the screen to make it easier to find mail.

On the left-hand side, underneath a list of your folders, is a section called Quick View, which allows you to quickly view mail based on several preset criteria. These include mail that you've tagged, mail with photos in it, mail with Office documents as attachments and mail sent from shipping services such as FedEx. Click any category, and you'll see only the relevant mail.

Filters, located just above the main mail screen, allow you to view your e-mail based on several other categories, including unread mail, mail from contacts, mail from Windows Live groups and others. Filtering is particularly powerful when combined with Quick Views. You could, for example, choose to see only mail with Office documents attached that were sent by your contacts. Or you could see all unread shipping updates.

Message threading is also improved by the addition of a Conversation View, much like you will find in Outlook 2010. It lets you easily see an entire e-mail conversation at a glance, including all messages sent and received, rather than hunting for them individually in your in-box, out-box and other folders. This seemingly small feature may be the biggest productivity enhancer in the entire Hotmail upgrade. It can easily save hours each month.

By default, the feature is turned off. To turn it on, you'll have to select Options --> More Options --> Conversation settings, select "Group messages by conversation" and click Save.

One of the niftier new features is the ability to view embedded media content directly within Hotmail, instead of having to go to an external site to view it. So if you're sent a link to a YouTube video, for example, you'll be able to view the video within Hotmail.

Finally, the Sweep feature cleans up clutter by allowing you to delete or move all marked mail in a folder, or mark an entire folder as having been read.

Improved security

Microsoft has added several new security features, most of which work behind the scenes, such as the SmartScreen antispam tool and what Microsoft claims is an improved spammer detection infrastructure.

The one security measure you will notice is the "trusted senders" feature, which puts a green safety logo next to legitimate senders that are often the target of phishing scams, such as banks. Hotmail identifies those messages that are from valid financial institutions and other targeted companies, making it less likely that you'll be victimized by a phishing attack.

Hotmail stays social

When you log into the new version of Hotmail, you don't immediately go to your in-box. Instead, you begin with a Hotmail highlights page (it actually lives on Windows Live rather than Hotmail) that grabs the latest information from your social networks, including Facebook and MySpace, as well as your contacts on Windows Live Messenger. (At this point, Twitter and LinkedIn are not available.)

This lets you see updates on Facebook without having to leave Hotmail. You'll be able to make comments on those updates, and they'll appear on Facebook, again without leaving Hotmail. You can even view videos posted on Facebook. You can't, though, post to your Facebook page.

If more services are added (including the ability to post to your Facebook page), Hotmail could become a central point for your communication on social networking sites.

Hotmail integrates with social networking sites in another very important way as well: It includes your contacts from those sites in your Hotmail contacts list. That way, you don't need to go to multiple places to find contact information; it's all right in Hotmail. A nice touch is that it categories your contacts for you as well, showing you contacts from Facebook, Messenger and so on. You can also view them all together, uncategorized.

When you view a contact from a social networking site, you'll see his contact information and can also jump directly to his page on, say, Facebook. I found one aspect of the way that Hotmail integrates with social networking sites confusing, though. When I was in Hotmail and was looking at a contact who is one of my Facebook friends, there was a message "You're not friends with Barbara. Add as friend." In fact, what it was doing was showing that I wasn't friends with that contact on Windows Live Messenger -- but it didn't specifically mention Live Messenger in the message.

Integration with Outlook

The newest version of Hotmail integrates with Outlook through the recently updated Microsoft Outlook Hotmail Connector. That's the good news.

The bad news is that all of Hotmail's new features aren't carried over to Outlook. For example, the only Hotmail contacts you'll be able to see in Outlook will be those native to Hotmail itself -- you won't be able to view contacts from social networking sites such as Facebook. And while you can see your Hotmail e-mail in Outlook, you can't use the Conversation View for it, which is odd, considering that Outlook 2010 has its own Conversation View. Perhaps in time integration will improve.

Other extras

There are a lot of other very nice extras in this version of Hotmail, including integration with the newly released Office Web Apps. When you're sent an Office document, you can save it to Skydrive -- Microsoft's free online storage service -- and from there open it in Office Web Apps, which is Microsoft's free online version of Office.

If you need heavier editing capabilities than are provided in Office Web Apps, you can then open the document in Office on your PC, although you'll need to be using Internet Explorer to do that. You can then save it back to Skydrive.

Speaking of attachments, you can send whopper-sized attachments in the new version of Hotmail if you want -- up 10GB in one message.

The way Hotmail works on mobile devices has also been improved. People who work in enterprises that use Exchange ActiveSync will be able to synchronize e-mail between their smartphones and the Web. Hotmail apps are available for BlackBerry and Symbian-based Nokia phones. (We weren't able to confirm whether apps for other mobile devices, such as the iPhone, are in the works.)

The bottom line

How does the revamped Hotmail compare to Gmail? In some ways, it's superior. The new Hotmail beats Gmail hands down for social network integration; Gmail also lacks the ability to view embedded media content from sites such as YouTube. For e-mail handling, while Gmail does an excellent job of that, I prefer the new Hotmail -- but that's strictly a personal preference. (For more on Hotmail vs. Gmail, check out my blog entry.)

This new version of Hotmail focuses largely on productivity enhancements such as improved mail handling. It's also now easily the most elegant-looking of any Web-based mail service. If you've never used Hotmail before, or swore off it in the past, now is the time to take a new look -- you'll likely be exceedingly pleased at what you find.

Preston Gralla is a contributing editor to and the author of more than 35 books, including How the Internet Works (Que, 2006).

This story, "Microsoft's Hotmail e-mail gets a makeover" was originally published by Computerworld.

Copyright © 2010 IDG Communications, Inc.

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