Hotmail, MSN Mail, Live Mail for a long time, and slowly but surely Microsoft continues to add features that bring the slightly clunky web email up to modern standards.
Unfortunately, they don’t let you add custom photos for any of your contacts.
In fact, the only built-in way to get your contacts to have a photo is to have them setup a Live ID on their email, and have them add an avatar.
Oddly enough, my Android phone has a handy feature of syncing contacts from multiple sources (like my Address book and Facebook/Twitter) and it will bring all of their information and photos together into one contact. It’s really handy, and easy to use. While browsing some of Live Mail’s options, I wondered if the same would be possible for my desktop mail.
It turns out that Live Mail has a similar ability to integrate 3rd party services into your contact list.
Most people in the USA use Facebook as their social networking platform, and Microsoft products and Facebook like to play well together as much as possible.
From Microsoft’s Help webpages:
You can get Facebook updates and chat with Facebook friends in Windows Live Messenger [or Live Mail] by connecting the Facebook service to Windows Live.
To connect the Facebook service
On a PC, go to the connect services webpage. You might need to sign in with your Windows Live ID.
On the Connect Facebook to Windows Live webpage, decide which activities you want friends to see in Messenger and in Facebook, and then click Connect with Facebook.
[Note: I was able to see contact photos with just the first permission of “See Facebook friends and their updates”]
Follow the instructions to complete the connection.
After that, I was able to see contact photos in Live Mail for anyone who I was also a friend with on Facebook (which happens to be most of my inbox.)
If anyone has a better / alternative way, please leave a comment!