I originally posted this in the gw2012 clients forum, but since then
I've upgraded our backend to 2014sp1, so figure we'll be on the gw2014
client in the not too distant future.

It's recently been brought up here the possible need to encrypt email
going out over the internet, and my boss believes this will happen, at
least for one department here, before too long. Bad thing about the
department that has been asking, they are some of our least computer
savvy users.......... :-|

I'm wondering the easiest / best way to do this. I've looked in the
documentation about using s/mime encryption, but this might be a
massive PITA with users having to keep track of certs on whatever
machines they use to access their GW account.

Anyone have any suggestions for this that are somewhat simple to set up?

I'm open to whatever options, even if it's a separate appliance to
house the encrypted email, etc.