Email encryption

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Dear Colleagues: What is the best way of detecting whether email messages are transmitted as cleartext? I want to determine whether our company email messages are encrypted or not when they are transmitted within and out of the corporate network. Thank you very much!
ASKED: January 5, 2006  8:26 AM
UPDATED: January 9, 2006  1:11 PM

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Most direct way is to put a sniffer on the mail server’s port (either with a hub, or by using a SPAN port on the switch) and watch some emails.

Your email administrators may also know, so it couldn’t hurt to ask them too.

Bob

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  • Develish
    Hi Bob's solution is plain, simple and easiest to you. Depending on your e-mail system, you can enforce mandatory encryption of messages. HIH, TIA, Regards
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  • Ve3ofa
    Email is normally not encrypted by the mail servers. Mail clients can encrypt the contents of the messages using digital ID's (configurable via group policy) but the header will not be encrypted just the contents. Digital ID's are also useful for confirming that the sender was indeed the person you recieved the message from and also that the message has not been altered.
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  • Layer9
    Simple Configure your perimeter switch to PORT SPAN (monitoring) and set a SPAN to include the port your outside interface is connected to and push all that traffic to the SPAN monitoring port. Plug a laptop running a standard Protocol Analyzer into the monitor port on the switch. If you don't have a Protocol Analyzer (Heaven Forbid) then just download Ethereal, which is free. Now you can see all traffic to and from your network. Simply create a simple SMTP filter in your Protocol Analyzer and set it to drop all other packets. Run a capture for an hour or so, depending on the level of activity you see, then look at the decodes. If you can read the emails, they are NOT encrypted. Peice of cake. Chris Weber Layer9corp.com
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