On Tue, Apr 28, 2020 at 12:18:14AM -0500, David Engel wrote:
> 
> We are a small company ahd IT is only one of his many jobss along
> with facilities, planning, project management and others.  He got IT
> because nobody else was willing to do it.  The explanation I got for
> not embracing an integrated, PGP solution was that he'd tried it
> before and that it broke wheneve MS issued an update to Outlook.

How many years ago did he try it?

GPG4Win has made vast improvements over the last several years.  As
long as the Windows versions in use are relatively current (i.e
post-runtime overhaul), then it should solve much of this.

If they're prepared for a bigger change that will solve it and still
let them use a GUI editor, then Thunderbird and Enigmail are right
there.  Hell, it was the default email for Sun Microsystems for years
and you need huge amounts of email to screw with it too basly (which I
have, which is why returned to Mutt/Neomutt and Emacs, though I
actually had that with TB too).

> I've shown an integrated solution to the two department heads
> repsonsible for most of the users.  One of them is my boss.  The
> problem is there is a lot of inertia behind the current, inefficient
> way they do things.  Everyone knows it's a pain but they all no how
> to do it and are reluctant to change.

Well, I guess that's a vehement *no* to the Thunderbird option.  😉

> To me, it's mind boggling how much productivity is lost.  The text
> for each encrypted email must be copied and pasted through the
> stand-alone PGP to encrypt of decrypt.  File attachements must be
> encrypted separately before sending and saved and decrypted
> separately upon receipt.  It's crazy.

Yeah, that's preety crazy and so unnecessary.  I mean it's not like
we're using PGP 2.x on old mid-'90s era systems.

Depending on what the full scope of what the ultimate end result is,
it might be possible to be streamlined and automated more, without
adversely affecting any other senders or recipients who know how
PGP/MIME works and that it's a Good Thingâ„¢ (like you).


Regards,
Ben

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