also sprach Kyle Wheeler <kyle-m...@memoryhole.net> [2009.12.05.0146 +0100]:
> >I haven't checked recently either; when I get some time, I'll fire up 
> >the ole XP virtual machine to check it out.
> 
> Unfortunately, all I have is MS Office 2000, which is too old to work 
> with GPG4Win.

I tried it, and GpgOL does indeed to proper MIME by now.

The major problem with GpgOL, despite its nice integration, is that
you can either enforce encrypt-to-all and require the users to
acknowledge unencrypted outgoing mails (which will be the majority),
or you can rely on them to encrypt mails manually. Since I don't
trust users and the first option will just train them to blindly
click away the dialogue, GpgOL is not suitable (although I will
write in to the team and suggest a policy-based approach).

I am now investigating GPGrelay[0], which has a few warts but looks
promising. It also does PGP/MIME and it has policy-based rules to
enforce encryption to certain recipients (when a key is known), plus
the ability to map wildcard addresses to keys.

0. http://sites.inka.de/tesla/gpgrelay.html

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