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1370

answers:

3

I have an Exchange 2007 configured with ActiveSync and RPC over HTTP.

Here are the things that work:

  • Outlook inside the network.
  • Mobile devices.
  • Outlook Web Access.

Only thing that doesn't work is:

  • Outlook outside of the network.

Whenever, someone is outside of the network trying to access their email via Outlook, they get prompted with their user name and password constantly. The machine can reach the network over HTTP, therfore the firewall configuration seems to correct. The machine also has the proper root certificate.

I am not sure what's going on here. Any tips will be well appreciated.

Thanks!

A: 

I think it's intended behavior. Outside the network, you're no longer on the domain, so the connection requires you to authenticate when you open outlook in order to connect to the right mail store.

Ian Jacobs
That is understandable. But it doesn't connect at all and Outlook constantly asks for User Name and Password.
When accessing OWA, if your email account has the primary address [email protected], but is hosted in the local domain mydomain.local and doesn't have a mydomain.local address then you get the same issue. I wonder if this is any way related...
BenAlabaster
Inside the network are you still using RPC over HTTP? If not, give it a try, that way you'll at least absolutely confirm it's not the external firewall blocking something.
Ian Jacobs
Ian, I think you were close here. The problem was the Exchange server was trying to authenticate the user when RPC over HTTP was used, instead of letting the Active Directory authenticate.
A: 

are you using firefox?

in firefox go to url : "about:config" page

then search for key "network.ntlm.send-lm-response" and set it to true

It might not help but sometimes my school proxy would prompt me for passwords like dozens of times in a few seconds and this key automagically solves that problem

Eric
+2  A: 

Okay, found it!

http://support.microsoft.com/kb/927612