I just spend an hour trying to let it work, and looking for the difference between two accounts which one of them have auto-updates and the other not.
It should be, for you:
Hoover over your display picture so that a smaal popup will appear.
In there you can click on "View your contact card"
In your own contact card click on "Share your contact info"
Now you're taken to an online page where you can enter the info and select who can see it.
Direct link to this page: http://profile.live.com/details/EditContact.aspx
The above is what _you_ need to do.
---
After that, your contacts need to 'subscribe' to (your) contact updates too though. However, after testing this several times in different ways I can't get this working either in Windows Live Messenger 2009.
Even not by enabling "Profile" and "Windows Live Messenger" in
http://profile.live.com/whatsnewwithyousettings/ for the account I whish to share info with. And not by enabling everything on
http://profile.live.com/WhatsNewSettings/ with the account I whish to view that info.
In Windows Live Messenger 2009, nor on the Live pages on the net, there doesn't seem to be an option anywhere to 'subscribe' to this kind of info anymore. The only way I can get this working is using Windows Live Messenger 8.5.
So, atm this is a mystery for me too. I can't find a way to subscribe to someone's contact info without using Windows Live Messenger 8.5.