My take on this is that it sounds like the minimum requirement is end to end secure 
connection over the Internet (as Andrey pointed out)...which does sound like a TLS 
candidate.  The problem with using PGP or the like is that you then rely on the 
customer (client) to encrypt the email.  If the requirement is that all transactions 
are encrypted then at least TLS enforces a secure transmission between two gateways.  
But I would also implement actual message encryption as well (again..PGP or the like). 
 So in the best case, you have an encrypted message traveling over a secure channel 
(public channel that is...this doesn't address what happens to the message while it is 
on its way to gatewayA and what happens to the message once it leaves gatewayB).  The 
worst case is that a client forgets to encrypt the email, but it is still transmitted 
over a secure channel (thus still meeting the requirement to transmit it securely over 
the Internet).

Best regards,

Steve

-----Original Message-----
From: [EMAIL PROTECTED] [mailto:[EMAIL PROTECTED] On Behalf Of Fyodorov, Andrey
Sent: Thursday, July 17, 2003 1:59 PM
To: Exchange Discussions
Subject: RE: Sending Secure Mail over the Internet


Ok I suggested it.

Because from what I read, they want to always send mail to the same destination in a 
secure way ("We want to send reports to the
State that contain information about our students")

In order to use PKI encryption, they would have to ask the recipient to obtain a 
certificate first, then get the recipient's public key from a digitally signed 
message, then always remember to encrypt individual messages.

With TLS, you set it up once and then start sending e-mail - the server does the job 
of encrypting the transmission every time.


If I had to send encrypted mail to many different destinations, I would sure go with 
PKI or maybe PGP. But when you are targeting the same place all the time, why not TLS?


-----Original Message-----
From: Johansson Patrick [mailto:[EMAIL PROTECTED] 
Sent: Thursday, July 17, 2003 3:20 PM
To: Exchange Discussions
Subject: RE: Sending Secure Mail over the Internet


Ok, maybe I've had a few too many beers but why in the world is everybody
suggesting TLS. It's a bother to set up and you have to do it with every
mail server you want to have secure communications with. Great, the
communications are secure but how about the actual e-mail? Correct me if I'm
wrong but the easiest way in this instance would be to just encrypt the
e-mail. Windows does provide CA and you can always get another certificate
from a known source. Another way to go is to use pgp or some offshoot of
that. I don't know but sometimes we (designers/administrators) get a little
over excited using technology we don't really have to use.
Well, just my 5 cents.

-Patrick

-----Original Message-----
From: Dickenson, Steven [mailto:[EMAIL PROTECTED] 
Sent: 17. heinäkuuta 2003 19:04
To: Exchange Discussions
Subject: RE: Sending Secure Mail over the Internet

If the sending and receiving mail servers, as well as any in-between support
it, TLS is an option.

Personally, I'd encrypt the e-mails using GnuPG.  www.gnupg.org

Steven
---
Steven Dickenson <[EMAIL PROTECTED]>
Network Administrator
The Key School, Annapolis Maryland 

-----Original Message-----
From: Bridges, Samantha [mailto:[EMAIL PROTECTED] 
Sent: Thursday, July 17, 2003 9:12 AM
To: Exchange Discussions
Subject: Sending Secure Mail over the Internet


Exchange 5.5 sp4
Windows 2000 Advanced Server
Outlook 2000 and XP clients


Hello All.

I work for a school district in Michigan.  We want to send reports to the
State that contain information about our students.  The information
contained in the email attachments must remain confidential and private.
Therefore, I need to provide a secure way of sending reports/attachments via
email over the Internet.

Any ideas or comments would be greatly appreciated.  

SSL only provides secure logons????....right???

Thanks for any help.

Samantha

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