Odd issue with VPN and Exchange So I needed a little advice as my Google-fu is failing me today. I have a user that when on his home network connects to his office via VPN connection. When this VPN connection is active, his Outlook suddenly stops working. No send, no receive, just a constant "trying to connect" and that incredibly annoying yellow exclamation inside of Outlook

Without VPN connected, his Outlook works fine. Now here's the real kicker...when he's in the office, and on the actual office network, his Outlook works fine. 

I have set up his mail profile outside of the office so that it won't auto-discover using the exchange server address and instead try to connect using an RPC address; but it has failed me there too. 

I am running into a wall here and would be happy to accept any advice or recommendations those smarter than me would kindly pass down. Thanks in advance!