I've been writing (and, on the podcast, talking) about my ongoing move to Web-based services a lot lately, but one thing I've had trouble settling on is an online contacts management system. (As noted in What I Use, I've had to temporarily use a local Outlook-based contacts list.) Despite my use of Gmail for email and Google Calendar for scheduling, Google's contacts management functionality (part of Gmail) is horrible and cannot be used as master contacts storage management. The problem is that Gmail doesn't allow you to disable the automatic addition contacts to your Contacts list (!!!!) So every time someone sends me an email--and yeah, I do get over 100 emails a day--they're added to my contacts list.

Bzzt. Game over.

I have this nagging feeling that I'm going to be moving to Live.com/Hotmail at some point. Part of the reason I went to Gmail/Google in the first place is that Microsoft wasn't ready to make Live.com email addresses public back in the Spring. (This should be happening soon.) As you may know, however, I spent the last couple of days in various meetings at Microsoft, and a few of them were with the Windows Live group. This rekindled a desire to examine how Windows Live handles contacts and, sure enough, it's quite good. Good enough, in fact, that I've already moved my master contacts list there and will continue to maintain it solely on Windows Live.

Here's the short version on how this works. While you can access Windows Live Contacts via http://contacts.live.com/ as expected, that URL actually resolves to the Contacts component of Windows Live Hotmail. You can add contacts to this database directly from Hotmail's Web interface, or through Windows Live Mail, Windows Live Messenger, Windows Live Mobile (on Windows Mobile or certain Nokia smartphones), or Microsoft Outlook via the free Outlook Connector. This is actually quite an amazing list of choices, and each of these applications is really just accessing the same cloud-based contacts database: If you make a change at any of these entry points, it will reflect in the others. (With one possible exception, see below.) Nice.

Getting the contacts into my Windows Live Contacts database was simple enough, too: Web Hotmail lets you import contacts from various CSV formats, sure, but I found it easier to simply install Windows Live Mail on my laptop and import directly from Outlook. I also used Windows Live Mail to funnel my contacts into various contacts groups (Personal, Work, and so on). Good stuff, and as expected, everything was pushed right to the Web.

Here's a tip, too. If you are making the switch to Windows Live Hotmail from another service, there's a free Windows Live TrueSwitch service that can semi-automate the process of getting your email history and address book copied over. It will even auto-notifiy contacts of your new address.

Overall, I really like what Microsoft is doing with the Windows Live stuff. And with an expected calendar update coming soon, my email and scheduling data might have a new home in the coming month too. 

Oh, I almost forgot: The one part of Windows Live Contacts I can't get to work is the user picture. Every contact can have an associated picture, but I can't figure out a way to add a picture in Web Hotmail or Windows Live Mail. I can add a picture in Outlook, but it doesn't appear to replicate back to the cloud. Anyone?