Windows Live Hotmail Review, Part 2: Windows Live Mail and Outlook Connector

When I wrote my original review of Windows Live Hotmail, the long-awaited update to Microsoft's venerable and hugely-successful Web mail service, I mentioned two other related Microsoft products, Windows Live Mail (formerly Windows Live Mail Desktop) and Outlook Connector. And I've gotten a lot of questions about whether I'd be reviewing these products, both of which let Hotmail users access the service via full-featured Windows applications. Truth is, I'd always intended to review both of these interesting products, but now that both are available in public beta form, it seems more logical to package these reviews together and tack them onto the original Hotmail review than to provide them separately. So here we are.

Windows Live Mail is Microsoft's successor to both Outlook Express and Windows Mail, the latter of which ships with Windows Vista. Microsoft describes Windows Live Mail as a superset of both of these consumer-oriented email products, and tells me that they will only actively develop Windows Live Mail going forward. That's just fine with me: Windows Live Mail is dramatically nicer than either Outlook Express or Windows Mail, and it includes a lot more useful functionality, especially if you're a Hotmail user. (This applies equally to msn.com and live.com accounts as well.) But Windows Live Mail isn't limited to just Hotmail accounts: This is a full-fledged Internet communications client, with support for POP3 and IMAP email, RSS feeds, and USENET newsgroups.

Outlook Connector 2007, as I think of the new version, is Microsoft's solution for integrating Hotmail email into Outlook 2003 and 2007, its premier email and personal information management (PIM) client. Outlook is what I think of as The Full Meal Deal, and if you want a full-featured email application, it doesn't get any better than this. Outlook natively supports Microsoft Exchange email, of course, but also POP3 and IMAP, like Windows Live Mail. When you install the Outlook Connector, you get Hotmail/MSN/Live.com support too. This used to be a paid feature, in that you could only get previous versions of Outlook Connector if you paid for MSN Premium, Hotmail Plus, or a similar Microsoft service. Now, the new Outlook Connector 2007 is free, even if you're using a freebie Hotmail (or, soon, Live.com) account. Ah, progress.

Both of these products are excellent, and both are unique in some ways. I'll say off the bat, however, that if you do already own Outlook, the Outlook Connector is the way to go: Outlook is just a premium experience. But in the world of free email applications, you could do a lot worse than Windows Live Mail. It, too, is a great solution, and probably a lot more interesting for the average consumer than the business-oriented Outlook. Let's take a closer look at each.

Windows Live Mail

Originally envisioned as an ad-supported email client for Hotmail users, Windows Live Mail has evolved over time and is now a much more impressive release as a result. The shipping version of Windows Live Mail--now available in a feature-complete public beta--offers seamless Hotmail/MSN.com/Live.com integration, as expected, POP3 and IMAP email functionality that rivals third party applications such as Mozilla Thunderbird (see my review), RSS support, USENET newsgroup support, and integration with various Windows Live services. If you use Hotmail and/or other Windows Live products like Windows Live Messenger, you're going to want to check this one out. Heck, if you use Internet email of any kind, you're going to want to check this one out.

Windows Live Mail sports the new Windows Live look-and-feel, which is heavy on the whites but with high-contrast bluish-green accents (Figure). Like newer versions of Outlook, and like the Web-based Windows Live Hotmail, the Windows Live Mail application is visually split into three mail columnar panes, from left to right: Folders, Message list, and Reading pane. Actually, there's an odd fourth pane called Active Search, too, but you can and should turn this off: Active Search is a weird front-end to Microsoft's Live Search service, and its real purpose is to deliver ads and sponsored results. Now that Windows Live Mail is no longer ad-supported, however, Active Search is like an unnecessary, vestigial tail. Did I mention you can turn it off?

In many ways, Windows Live Mail works like Windows Live Hotmail, and if you're familiar with the new version of that Web service, or with traditional email clients like Outlook, you'll have no problem getting up to speed. Architecturally, Windows Live Mail is based on Outlook Express and Windows Mail, so some UI bits, like the Options dialog (Figure), and the files Windows Live Mail creates, like the .eml email files, might look familiar. What's old is new again.

I used Windows Live Mail as my primary email client for a few weeks and had absolutely no issues. I like some of the customization bits: You can color-code the folders for each email account you configure and apply a Windows Live color scheme to the entire application so that it matches your other Windows Live applications and services. (I happen to like the black color scheme quite a bit.) On the other hand, Microsoft isn't taking the logical integration approach by pushing whatever Windows Live Mail color scheme you configure out across all services and products automatically. How nice would that be?

Speaking of integration, Windows Live Mail is particularly useful if you're a Windows Live Messenger user. It can be configured to automatically log you onto Messenger whenever you launch the mail client. On the flipside, if you see an email alert in Messenger and click it, Windows Live Mail will launch instead of forcing you to use the Web client. The Contacts portion of Windows Live Mail, which is also a native Windows application, integrates your traditional email contacts with your Windows Live Messenger contacts list, too. A Blog button on the application's toolbar lets you publish the current message to your Windows Live Spaces blog.

As a modern email application, Windows Live Mail supports instant search, which works wonderfully. There's also an Outlook-like search folders feature, though I haven't found a way save email searches as dynamic virtual folders. Instead, stock saved search folders, like Unread email, Unread from contacts, and Unread feeds, are available.

So why would you want to use Windows Live Mail instead of the Windows Live Hotmail Web service? First, and most obviously, Windows Live Mail works offline. So you can sit on an airplane or in some other disconnected location, navigate through and read your email, respond to emails, write new emails, and perform other actions that would be impossible with the Web client while offline. Once you're online again, all the pending email is sent and everything is synched up again, just as with Outlook and other traditional email clients.

Windows Live Mail also features email account aggregation, so that you can easily access email from two or more accounts (be them Hotmail/Live.com accounts or any combination of POP3 and IMAP accounts), all from the same location. With Web-based email services, you might need to have a different browser window open for each service.

From a safety perspective, Windows Live Mail also provides protection against phishing attacks, viruses, and other malware. This works for all account types, so even though your Hotmail account may be protected by server-side AV scanning, your POP3/IMAP accounts might not. And if you're into the Windows Live stuff, the integration pieces are quite interesting as well.

Windows Live Hotmail is free and available for users running Windows XP with Service Pack 2 (SP2) or Vista (any version). If you're currently using Outlook Express or Windows Mail, I strongly recommend upgrading to this product immediately. It is nicer looking, works well with non-Hotmail accounts, and offers much more useful functionality than its predecessors. I like it quite a bit.

Outlook Connector 2007

While Windows Live Mail supplies a surprising nice email solution for consumers, business and power users know that Outlook is Microsoft's premium email experience. There's just one problem, if you're a Hotmail user: Outlook isn't natively compatible with Hotmail (or MSN.com and Live.com mail).

This sorry state of affairs is corrected with the release this week of the new Outlook Connector, or Outlook Connector 2007, a small Outlook add-on that makes Hotmail and MSN (and, eventually, Live.com) email accounts first-class citizens in Microsoft's top dog email application. (Versions of the Outlook Connector have actually been floating around for years, but they were previously made available only to those who paid for premium versions of MSN or Hotmail.)

Installation is a breeze, and when you boot up Outlook again, you'll be prompted to enter information about your Hotmail account. Curiously, this doesn't happen through Outlook's built-in account wizard, but rather through an even simpler dialog that only requires your user name, password, and then name you'd like to use for outgoing mail (Figure). (And while you will see your Hotmail accounts later listed in Outlook's native Account Settings dialog, when you change settings, you'll still return to the new, simplified, Outlook Connector dialog.)

By default, Outlook Connector synchronizes your Web-based Hotmail account with local folders in Outlook, treating Hotmail, in a sense, like an Exchange Server. Changes you make locally are eventually (but not, in my experience, immediately) made up on the server, and vice versa. This is an important concept to understand: Hotmail email accessed through the Outlook Connector is not only downloaded to the local PC, as it would be with a POP3 connection. Instead, Outlook Connector maintains copies of all your email activity both on the Web and on the client. So you can move back and forth between the two and not worry that something will be lost. You can also, of course, access your Hotmail-based email and contacts offline.

Each Hotmail/MSN/Live.com account you configure in Outlook will appear as its own discrete top-level folder hierarchy in the Mail Folders list, or, in Outlook parlance, as a separate Outlook data file (in this case, offline folders instead of personal folders). Their found in the same place in the local file system (in a hidden location by default) as personal folders, though the Account Settings dialog doesn't tell you that. Since everything is synchronized with the server, however, this isn't as critical as it is with email and other Outlook information that is downloaded and stored locally.

In use, Outlook Connector makes Hotmail a first-class Outlook citizen as hoped, and if you're familiar with Outlook, you'll be able to jump in immediately. Any folders you created on the Web-based version of Hotmail are pulled down, as expected, and you can now use all of Outlook's excellent email tools to manage your mail. A new Outlook Connector menu item in Outlook provides a front-end to many Hotmail and Windows Live ID-related options, though most push you out to a Web page. The Sharing option, curiously, provides Outlook-based UI for managing which of your contacts can access your shared Hotmail calendars.

Unlike previous versions, Outlook Connector 2007 is free and available for users running Windows XP with SP2 or Vista, and Outlook 2003 or 2007. This one's a no-brainer: It works nearly-seamlessly with Hotmail and if you're looking for the ultimate way to integrate your work and personal email into a single location, this is the way to go.

Final thoughts

Both of Microsoft's new Hotmail-related desktop email tools are top-notch, but deciding between them is simple: You either have Outlook or you don't. If you do, snag the excellent Outlook Connector and enjoy Microsoft's premium desktop email experience. If you don't, Windows Live Mail is a high-quality, attractive, consumer-oriented email program that's much nicer than Outlook Express and Windows Mail. It's technically on-par with Mozilla Thunderbird and arguably a lot nicer looking too. Both the Outlook Connect and Windows Live Mail are fine choices for individuals looking for desktop-based access to Hotmail, and both are highly recommended.