I have outlook 2011 on my mac configured for Exchange, Gmail, and Hotmail. However, depending on where I am connecting from, Gmail and Hotmail will not connect sometimes likely due to the network preventing particular port connections.
During these times, Outlook continues to annoy me with a message that it cannot connect. If I choose to do this offline, it will take all the accounts offline which is not necessary. The accounts are configured correctly and will connect when i move to a different network.