It's always "since latest update"
@Outlook.com / Hotmail was seriously screwed up from September 23 and only reported as "fixed" recently.
I just tied my @hotmail.com account, both incoming and outgoing servers are checking fine.
Can you post what error message / issue you're seeing with the outgoing server? I really can't see your phone from here
Oh, and the right outgoing server settings:
smtp-mail.outlook.com
STARTTLS
port 587
If you get "connect error" then please try
smtp.glbdns2.microsoft.com
STARTTLS
port 587