Outlook 2010 unable to send mail when connected to VPN

[dmcmillen]

Win 7, 64 desktop, AMD 8350 8-core, 16gb, Linksys EA8300 router, Arris SB6190 cable modem, xfinity hi-speed int

I am running IPVanish (latest version) & Outlook 2010. Outgoing smtp server is smtp.office365.com and outgoing server is configured as 587, TLS. Outgoing server requires authentification/use same settings as incoming mail server.

IPVanish with L2TP, OpenVPN Port 443.

This seems to be a common problem that I see in the forums all the time and affects multiple versions of Outlook (and other mail providers, as well) and multiple VPN providers. Right now my only solution is to disconnect VPN before sending mail.

Here are the things I have tried:

• Tried different VPN protocols/ports
  
• Tried logging on in Outlook specifying username and pw
  
• Tried logging on in Outlook using SPA (didn't expect that to work)
  
• Tried logging onto incoming mail server before sending mail
  
• Tried adding 127.0.0.1 smtp.office365.com to hosts file

What I would like to do now is to add a route to force using the regular network instead of the VPN network for smtp.office365.com. The problem is that MS uses multiple ip addresses; I'm sure there are farms of servers. Here is the ip resolution from ipaddress.com:

When I ping smtp.office365.com it returns an ip (either vp4 or ip6) which is different. See ping here:

I'm pretty much at a loss at this point as what to do. route print or netstat -r are not helping me but I am a bit out of my element here so I would appreciate any help. Disconnecting VPN before sending mail isn't the end of the world, just a bit of a pain, especially if I forget and come back hours later to see unsent mail.