I have a number of users on Outlook 2011 that are having issues working between the office and remotely when attempting to connect to an Exchange 2010 server.

Within the office, users must be connected via ethernet. Internally, the mail server is internal.mycompany.com. Externally, it's external.mycompany.com

When the user is connected to the internal network, only internal.mycompany.com is reachable. external.mycompany.com is not. When working remotely, the opposite is in effect. (I don't know why this is the case, I'm just the support grunt). 

When attempting to configure Outlook 2011 and the user is connected to the internal network, auto discover seems to try and access external.mycompany.com rather than internal.mycompany.com.

No matter if I allow or deny the request, eventually Outlook will prompt for me to enter the server address manually. When I add internal.mycompany.com, it connects. When the user goes offsite, it switches to external.mycompany.com.

But, when the user comes back to the office, Outlook fails to switch and the user cannot connect.

Apple Mail does detect the correct server details for both internal and external servers, avoiding the issue. 

Can anyone shed any light on the issue? At first, I thought it might have been an Exchange-related issue but as I can get mail to work within Apple Mail, I'm leaning towards an Outlook 2011 issue. 

Is it possible to manually specify both internal and external servers and turn auto discovery off? 
We have mac book pro with outlook 2011 autherised version.I configured the exchange mail from internal network after network cable plugged.Put the local server name and its working..Whenever i reached at home,trying to connect through home internet.Its not connecting.Then i created one more account with the server name as webaccess server name, it is connected and at the office the second account is not connecting..So pls advice to me for create an account which has to be worked on internal network and at my home network.
HI guys,
I'm trying to set up outlook for a client on their mac.
the version of outlook is 2011 for mac. it is with an exchange server. I am setting this up on an internal network. (using a VPN with VPN Tracker 6)
I have internet connectivity though the VPN and can Ping the mail server's URL.

However,
whenever I try to send/receive with outlook, I get error -17199

what am i missing?