Can you please assist on the issue on sending email using Outlook 2011 on MAC? I was not able to send message larger than 5MB using outlook for mac 2011 with an E3 Office365 subscription. I am able to send thru our Webmail however on MAC im getting the error message. 

An operation to the server timed out. The server may be down, overloaded or there may be too much net traffic.

When I send a file with small attachment it will go through. 

thanks in advance for your assistance.

Michael Ancheta.