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recommendations for email encryption for exchange

Posted on 2011-03-16
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we have a need for encrypting emails that are sent from our exchange 2003 server so that outside recipients must somehow decrypt the emails to read the contents.  so far the only thing I have seen that will do this is a hosted email service where the recipients would need to create an account and log in to retrieve their emails.  

while it has the advantage of notifying the recipient that they have a new encrypted message, this is essentially the same as me encrypting internal emails and then creating an account for the external recipient and having them log in to retrieve their email.  of course it would require a lot less effort on my part to use the hosted service but would include a monthly price tag and significant startup fees as well.  

so I'm looking for other options, preferably something that is made to work with exchange 2003... any suggestions?

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Question by:cymrich
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by:waleeda
waleeda earned 167 total points
ID: 35151595
check one good product  called IronPort from Cisco
http://www.ironport.com/
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by:brota
brota earned 167 total points
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I second the IronPort.
Or if it is specific domains you could use TLS
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Dave Howe earned 166 total points
ID: 35161038
Ironport is what is called "oracle based encryption" - in that the recipient need not already have an encryption key in order to receive encrypted mail. While outlook (and to a certain extent exchange) has built-in support for using s/mime (x509) keys for encryption, the requirement that you get the encryption key to the *sender* of the email is usually where all the hard work comes in.  waleeda's recommendation of an ironport then (which is indeed a subscription service) is probably the easiest.

brota raises an interesting possibility - with exchange versions 2007 and 2010 you can *require* that the receiving server support the "TLS" encryption scheme - this is the same scheme that is used for https websites, and encrypts not the email, but the conversation between servers. In this solution, the mail is and remains unencrypted, but the link from your mail server to the recipient's is secured with encryption, hence the mail is delivered encrypted (consider ironport as delivering an encrypted telegram, but TLS as delivering a perfectly normal letter, but locked in a steel case and couriered to the recipient, who has the only key)

either are good solutions :)
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by:cymrich
ID: 35168521
unfortunately we don't currently have the option of upgrading to 2007/2010 for our exchange.  I will look in to ironport though and see if it looks feasible.  thanks for the suggestions.  
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by:Dave Howe
ID: 35168668
well, pre-2007 can handle tls, but can't insist on it. however, if that is what you want you could "front" your outbound traffic from exchange with an open source mailserver such as exim that CAN insist on TLS - that is a cheap alternative. you can even run exim directly on a exchange server if you use cygwin.
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by:waleeda
ID: 35168731
Ironport is very nice applaince we are already using it and it supports high availablity, its cisco products
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by:Dave Howe
ID: 35168785
the ironport appliance is very nice indeed - I work for one of their resellers - but the clustering / HA is not particularly good. no doubt they will fix that in time :)
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by:waleeda
ID: 35422627
why i didnt get any points.?!!!!!
i was the first one who answered about ironport
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by:Dave Howe
ID: 35422640
I agree - waleeda may have had a fairly short answer, but given part of my answer was an amplification of his, he deserves at least some points.
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