Ah, got it - and, I guess that would depend on which way the wind is blowing.  

Interestingly, at one point in time their music on hold for support started 
with Gene Autry's Tumbling Tumbleweeds. 

---------------------------------
Sent from my BlackBerry Wireless Handheld

----- Original Message -----
From: Jeff Brown <[EMAIL PROTECTED]>
To: MS-Exchange Admin Issues <exchangelist@lyris.sunbelt-software.com>
Sent: Thu Apr 24 07:06:07 2008
Subject: Re: Email Certificates

I think I understood most of what you were saying.  I was referring to 
tumbleweeds when I said off-site. (that really is off-site, right?)


On Wed, Apr 23, 2008 at 6:10 PM, Don Andrews <[EMAIL PROTECTED]> wrote:


        Didn't mean to imply off-site – both the SMIME proxy and Secure 
Messenger solutions are internally hosted – in fact on the same set of servers.

         

        ________________________________

                Thanks for the input.  the off-site solution seems to be very 
popular.

        On Wed, Apr 23, 2008 at 3:23 PM, Don Andrews <[EMAIL PROTECTED]> wrote:

        Yep – SMIME is a client to client protocol – each client will need 
their own certificate, then will need to do a certificate exchange etc. etc. – 
and bottom line is the sending client is required to ensure that they send 
encrypted after all that.

         

        Some of us have gateways that act as SMIME proxies for our internal 
users freeing them from this burden, but there is an administrative overhead to 
getting it all working the first time – and the external client still has to do 
their end – the major advantage is that the server can ensure that outgoing 
messages are always encrypted and warn the recipient of unencrypted inbound 
messages.

         

        Given the overhead of SMIME encrypted email, some have opted for a 
browser based secure FTP-like solution – we use Tumbleweed's Secure Messenger 
for this.

         

        ________________________________

                From: Troy Meyer [mailto:[EMAIL PROTECTED] 
        Sent: Wednesday, April 23, 2008 12:54 PM 

        
        To: MS-Exchange Admin Issues

        Subject: RE: Email Certificates 

         

        Uh-oh   that throws a wrench in the bucket, if we cant actually 
communicate with the admin of the email server on their end (cox) we may be in 
trouble.

         

        If they are using the standard cox server at mx.west.cox.net 
<http://mx.west.cox.net/>  (or mx.east.cox.net <http://mx.east.cox.net/> ) then 
transport encryption may not be possible ( a quick telnet into that address 
does not accept a TLS or STARTTLS command, its pretty plain jane).

         

        So options would be setting up SMIME User certificates which is a 
little more work and would require some user training. Or if the other company 
moved to a different (infer better) email hosting provider then they could 
except TLS encrypted email.

         

        No easy options L

         

        -troy

         

         

        From: Jeff Brown [mailto:[EMAIL PROTECTED] 
        Sent: Wednesday, April 23, 2008 12:04 PM 

        
        To: MS-Exchange Admin Issues

        Subject: Re: Email Certificates 

         

        Any way to set that up from my E2K3 domain to their Outlook client?  
Their email is hosted by an ISP and is pop3. (@cox.net <http://cox.net/>  email 
address)??

        On Wed, Apr 23, 2008 at 12:06 PM, Troy Meyer <[EMAIL PROTECTED]> wrote:

        Jeff, if you mean simply making sure that the general internet cant see 
the messages and you aren't worried about encryption once they reach the other 
companies servers, it should be simple; assuming the other company's MTA will 
accept TLS encryption, you can create a new routing group connector to that 
domain and require TLS and that should encrypt all transport traffic between 
your locations (including BB traffic because all BB sending occurs through your 
exchange server).

         

        I haven't configured 2003 in a while, but I believe that should be all 
that is required.  Michael, Kevin, any input?

         

        -troy

         

         

        From: Jeff Brown [mailto:[EMAIL PROTECTED] 
        Sent: Wednesday, April 23, 2008 9:57 AM 

        
        To: MS-Exchange Admin Issues

        Subject: Re: Email Certificates 

         

        Thank you very much.   I will look at that information as time allows.  
We are running E2K3 and BES 4.1.  Main concern at the moment is that we find a 
way to send email from BB's to vendors OUTSIDE our network in a secure way that 
is readable by them.

        On Wed, Apr 23, 2008 at 11:30 AM, Troy Meyer <[EMAIL PROTECTED]> wrote:

        Hi Jeff,

         

        You really need to understand PKI with regards to how it works before 
you can really implement encryption.  I assume you are running some flavor of 
exchange and are looking to encrypt messages, have you looked at this:

         

        http://technet.microsoft.com/en-us/library/bb123466(EXCHG.65).aspx

        http://technet.microsoft.com/en-us/library/bb124155(EXCHG.65).aspx

         

         

        It references 2003, but SMIME/PKI is not largely different between 
applications or exchange versions.  From the sounds of your email I think you 
are confusing different types of encryption, eg:  yes you can use transport 
encryption with SSL certificates that are trusted by all platforms/browsers 
without interchanging keys (because in essence the public key has already been 
accepted), but if you are looking for message encryption, you will need USER 
certificates, which will still need to be accepted by clients.  So when you 
tell exchange to encrypt all outgoing email, you are encrypting the transport 
from Exchange to the other server, but you are NOT encrypting the message 
itself. (Yes you can tell Exchange to encrypt all outgoing, and yes you can 
tell Exchange to encrypt transport to only a specific domain.)

         

        So really it comes down to what exactly you are hoping to do, do you 
want full message encryption or simply to prevent sniffing of traffic on the 
open internet?

         

        As for blackberry, you can do both here as well.  If you are running 
this you can sign/encrypt individual messages using SMIME.

         

        
http://www.blackberry.com/btsc/search.do?cmd=displayKC&docType=kc&externalId=KB10199&sliceId=SAL_Public&dialogID=55761554&stateId=0%200%2055759922
 

         

        If you are running BES then your communication is encrypted until it 
comes back to your home exchange server, and then it will travel as a normal 
message (ie if you are encrypting outbound traffic it will travel over that 
tunnel, otherwise it becomes a plain text outbound.)

         

         

        Hope that helps, it's a lot of information, but security/PKI/SMIME 
deployments can be difficult if you don't break down exactly what you (and the 
business) want.

         

        -Troy

         

         

        From: Jeff Brown [mailto:[EMAIL PROTECTED] 
        Sent: Wednesday, April 23, 2008 5:40 AM
        To: MS-Exchange Admin Issues
        Subject: Email Certificates

         

        I need help correcting filling in/correcting holes in my understanding 
of email certificates and how they work.

         

        I purchase a well known cert for my domain so that I can send encrypted 
email over the public domain.

         

        Because I laid out the money for this well known cert, I don't have to 
exchange certificates with folks outside my domain in order for them to read my 
encrypted email, right?

         

        In Outlook, there is a checkbox to encrypt outgoing email.  Is there a 
way on the org. level to say all mail sent to anyone @thisorg.com 
<http://thisorg.com/>   outside my domain should always be encrypted?

         

        Because I paid the big bucks, can we just set it on the domain level to 
encrypt ALL outgoing email?

         

        Will this well known cert allow my BB users to send encrypted email to 
folks not in my org?

         

        TIA,  I really appreciate those of you who are able/willing to 
"educate" the poorly informed.

         

        Jeff

         

         


         


 


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