I've noticed a unique problem with Outlook 2011...and it's the only gripe I have....when you are traveling and staying at a hotel, Outlook just can't get any emails to go out. However, Mac Mail works just fine and I can get emails to go out. Initially, I thought this was because the hotel blocked SMTP port 25, but Mac Mail worked just fine without changing the port number, authentication, SSL, etc, etc. I fought with Outlook 2011 for an hour...changing port numbers, turning authentication on and off....SSL on and off....never got it to send out emails. Anybody else run into this problem? I hate to dump Outlook, but Mac Mail seems to be more dependable.