Inline PGP Within HTML

[David Engel]

On Mon, Apr 27, 2020 at 12:32:05PM -0500, Derek Martin wrote:
> On Sat, Apr 25, 2020 at 09:46:48PM -0500, David Engel wrote:
> > Hi,
> > 
> > My company uses PGP/GPG when sending sensitive material through email.
> > Unfortunately (for them and me), most people use Outlook and our IT
> > guy refuses to install any Outlook plugin for them to properly handle
> > encypted emails.  
> 
> I know this doesn't really help you, but your real problem is you need
> to fire your IT guy.  As a former one myself, the role of IT should be
> to help users solve their legitimate business-need cases of technology
> issues, and yours has failed.  He needs to be taught that is job is to
> aid, not hinder, the business achieving its goals.

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.

> Barring that, you need to seek out those with enough political power
> to force your IT guy to do what you need, and convince them to do so.
> Everyone has a boss...  And if you lack access to those people, it's
> just a matter of finding someone you do have access to who does, who
> will sympathize, or at least empathize, and make your case for you.

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.  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.

On Mon, Apr 27, 2020 at 01:46:26PM -0400, Scott Kostyshak wrote:
> On Mon, Apr 27, 2020 at 12:32:05PM -0500, Derek Martin wrote:
> > On Sat, Apr 25, 2020 at 09:46:48PM -0500, David Engel wrote:
> > > I've given up politely asking people to remember to send email as
> > > either both text/html and text/plain or just text/plain when sending
> > > to me.  It's a losing battle. :(
> 
> You've given up *politely* asking? Meaning you are now asking
> impolitely? :)

I do have to keep working with these people. :)

> > Yeah, I've been trying to explain this to some folks around here
> > recently, but not having much success.  You have my sympathy.
> 
> Agreed. It is frustrating. But Derek, please don't give up! Even in the
> worst case scenario, we can slow the acceleration. I especially take the
> time to choose the battles where the email is from an automated system.
> I contact the support and send something like the following:
> 
>   Could you please modify your automatic emails to also send a
>   plain-text version in addition to the HTML email? This is easy to do
>   and most professional emails provide a plain text version (this is
>   called multi-part MIME).
>  
>   If this doesn't make sense to you, please forward this request to your
>   tech team.
> 
>   Thanks for your time!

I have essentially done this but the problem keeps reoccurring.  I
think part of the problem might be Outlook itself.  I vaguely recall
seeing something about Outlook only sending both text/plain and
text/html when those are the only two parts.  If another attachment is
included, I seem to recall that one of the text parts got dropped.  I
could be wrong, though.

I'm considering trying the polite approach again but this including
the pointer to the integrated solution I tested.  Maybe I can start
the change from the bottom up.

David
-- 
David Engel
david at istwok.net