Outlook 2013 does not connect to Office 365 server when connected to SSTP VPN

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Involved: Windows 8 Pro x64, Outlook 2013 x64, SSTP VPN with CHAP auth hosted by Windows Server 2008 R2 x64, mail hosted by Office 365

If I'm not connected to the VPN, outlook connects to o365 and works as expected. When I connect to the VPN, outlook drops the connection. I also have outlook.com mail set up with EAS, and it works as expected both on and off the VPN.

After investigating the connection status in outlook (control-click on tray icon, connection status), I see that when it's working (not connected to the VPN), the connections for o365 have a proxy server (resolvable and pingable) and server name (not

resolvable, not pingable, as expected). When I connect to the VPN, the connections disappear and reappear, but with blank proxy server fields and server name fields identical to what they were before connecting.

I can request and get account autoconfiguration information when connected to the VPN...

And I just realized that the DNS for the local network I'm testing it from matches the domain name for the email. Outlook probably thinks I'm connected to the internal network when I'm connected to the VPN. Is there any way to tell it I'm not

on the internal network?

 

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