if the mail can no onger be delivered?

Can Hotmail ask and then do this automatically if the recipient is not deliverable

Contact format was changed in Hotmail recently.  I'm having trouble getting new ones entered.  After hitting 'apply' they are then not coming up when trying to send and email.  Also one I put in wrong, went in and deleted it and put in the new one, but the old one keeps coming up still.  It won't let me put the new one in.  The emails are showing in the contacts section but not when I try to do an email.  Why.... Help...
The search option to find other emails from the same contact comes back none found?
I cannot add my contacts to Windows Live Messenger on my Windows 7 laptop. 
Messenger was working fine a few days ago but then my contacts disapeared. 
I've tried reinstalling the latest version of Messenger and I also tried an older version but it's still the same. 
Anyone have any ideas?. Works fine on my Vista PC, Android Tablet and Mobile, the problem is just with my laptop.

If you put in the contacts email address in the Search contacts bar provided there window appears and gives you the option to add a contact as a friend, all you get when you click on that option is a web page opening and saying the contact has already been invited. 
If you click on add a contact from the option provided all you get is you have previously added a contact who uses this instant messaging address.

I can see my contacts online if I click on the People link but I cannot see them in messenger on my laptop.
I'd appreciate it if anyone could help me.
Thank You :)
I deleted a contact but when I go to new mail to, its still there.  How do I get rid of it?
I don't have my groups listed anymore. I want to be able to send an email to my entire group but I can't get to my group. How do I get to them? Help!
I need to delete some contacts, but they don't pull up when I click under the People tab. When I click "To" in the send field of the email, they DO show up. How can I delete them from my contact list?
I don't know if this is specific to Mountain Lion or not but i've recently noticed my Outlook and sync slowing down..

Thought i would do some checking.. i have 13 contact categories and in total 8,516 contacts..
Now i know i don't actually have this many contacts in Outlook.. should be around 2,300 to 2,400 in total..

So i deselected all the tick boxes and went through each one.
on the No Category box it says i have 4,764 contacts
They are all blank..

I deleted them and then a message came up saying i had some sync conflicts..
Then all of a sudden they started coming back.

What is the sync process with itunes, outlook and an iphone ???
All i want is for my Outlook contacts to be on my iphone

But from what i gather, the contacts go from outlook, to address book, to itunes, to iphone ???
How does this all work and what do i need to change to have contact details go one way only - outlook -> iphone and that's it ???

This is really annoying as i changed over to Mac for work and it appeared everything is working fine..
Now it's causing my problems..
I have several groups, but some of the contacts have been dropped out inadvertently.  How do I add a contact to a group?
I am having trouble sending emails.  My contact list is missing.  I can't auto popluate addresses by typing part of it in.  I can't access the contact list by clicking on the To: button and when I go to the menu option for Contacts it doesn't find my contacts.  Something is very wrong, it has been like this for 2 days.  How do I get access to my email contacts ASAP!