My understanding is that you shouldn't be accessing Tor through anything but 
anon-whonix or a copy of that VM (this might be wrong). I'm not sure what 
metadata your work applications may leak that will compromise the anonymity of 
your Tor connection. You should do some reading up on whonix.

But if you don't trust Tor more than https, when are you using it?

If you want to create a secure connection to your office, I think the best tool 
to use is VPN.

I'm not sure what kind of trigger you're looking for, but I'm sure that you 
could write a script that will make it happen.

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