It depends what you think the risk is.  Are you protecting internal emails 
between staff?  External emails to trusted (known) partners?  External emails 
to anyone?

For external, TLS is the easiest answer if your threat is mail in transit.  
Opportunistic should just be set anyway.  Mandatory would be between agreed 
organisations.  There are mail gateway appliances you can buy which can define 
policy based encryption too.

For internal and the ability to email anyone, anywhere with encryption, you may 
want to look at S/MIME or PGP Mail.  Fairly straightforward, but you will have 
a user education piece to go with it!  This is the only way of ensuring user to 
user encryption rather than just in transit.

And no, it’s not all that paranoid at all.  In fact, most regulated industries 
have been doing one or all of the above for a long time …  ☺




a

CLS Classification: Confidential Information

This email was classified by Davies, Alan on 26 February 2015 09:31:19.

From: [email protected] [mailto:[email protected]] On 
Behalf Of Kennedy, Jim
Sent: 25 February 2015 20:10
To: Micheal Espinola Jr
Subject: RE: [Exchange] Email encryption

It helps to a certain point. I just don’t think with all the government data 
dumps being done that we have any real privacy on the net anymore.  So your 
encrypted email is only as good as the various governments that are copying it 
and storing it currently.

So probably pretty good and worth the effort, but not as good as perhaps your 
users think it will be.

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Steve Ens
Sent: Wednesday, February 25, 2015 2:58 PM
To: Micheal Espinola Jr
Subject: Re: [Exchange] Email encryption

Tell me more Jim, why are you cynical?  Because they can get in anyway?  Or 
what?

On Wed, Feb 25, 2015 at 1:47 PM, Kennedy, Jim 
<[email protected]<mailto:[email protected]>> wrote:
They are right, but encryption won’t help. I suggest written notes sent via 
trusted employee with said employee videotaping the recipient eating the 
message after reading it.  Then shooting the delivery guy when he gets back.

Sorry, couldn’t resist. My cynical hat is on today.

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]<mailto:[email protected]>] 
On Behalf Of Steve Ens
Sent: Wednesday, February 25, 2015 2:18 PM
To: Micheal Espinola Jr
Subject: [Exchange] Email encryption

The news gatherers think that their messages are highly sensitive and don't 
trust regular email any longer.  Is anyone encrypting?  What is the preferred 
method?  This is new to me.
Thanks
Steve

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