How to route gmail via VPN

How to route gmail via VPN

How to route gmail via VPN
I hope someone can help me with this. Here's the situation:
My wife has a TP. She wants to use it in the wild with unsecure wireless hotspots. I'm not comfortable with that as her gmail and facebook passwords will be broadcast out in the open.
What I've done is to set up an OpenVPN server (a Windows 7 x64 box) at home and installed the OpenVPN app on her TP. I have also installed the ProxySwitch app. I can now forward, via proxy, her web usage back to my home VPN server and onto the Internet from there. I can also do the same, via tunnels, with her non-gmail based e-mail (POP) accounts. That all works nicely. However...
Here's the problem. I can not forward her gmail (IMAP) communications via tunnels over the VPN. The response from the e-mail app is that the host certificates do not match. I assume that to be true since the e-mail app is looking for gmail and it is finding my home VPN server first. Interestingly, I do this with my Windows laptop and Outlook seems to have no problem with it. Works like a champ. I need to keep this IMAP as that is where her contacts and calendars are.
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