Sendmail/SMAIL Snooping Setup with Smart Server

Posted on 1998-12-08
Last Modified: 2010-03-18
   We have a network mail server provided by our internet provider. 25 Win98/NT machines send POP3 mail directly to the providers server. We need to be able to snoop and monitor all emails leaving the office. We have 2 Linux Boxes,  A Samba server and a router box. We also have 2 NT Servers... I need to setup some sort of system where the 98/NT machines can connect to the POP3 server where the mail will be carbon copied to a email moderator before being sent to the ISPs server...
How can this be accomplished?
I have heard of smart servers but I don't fully understand, nor do I know where to start.
Please help.
Question by:lgalea
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Expert Comment

ID: 1587818
Are you working for the big brother ?? I don't want to be noisey, but it certainly is an invasion of privacy. The employes might sue you unless you must specify that all e-mail/communications might and will be monitored by you. You could install a sniffer on the wire copy all tcp packets for port 25. Install a firewall between you & your ISP thus forcing your employees to use your mail gateway. Thus very easy to make copy of e-mail. Setup your router to filter all tcp packets to port 25 only leaving a mail gateway, 1 machine capable of going outbound on port 25. The install a mail server, thus forcing them to use your mail gateway .... Anyhow, becareful, lawyers fees are not cheap.

Author Comment

ID: 1587819
n0thing... Thank you very much... But how do I setup the mail server to cc all messages.... I know this sounds dirty... but more so it isn't to see what is being sent but who it is being sent to.. (for security issues)...

Accepted Solution

n0thing earned 200 total points
ID: 1587820
Basic sendmail logs will log the sender/recipient. So you'll see the the logs the sender/recipient pairs. As far as the content of the mail. If the users know their messages are logged, they'll simply encrypt the before sending it. There is nothing you can do about it. As far as cc's, you'll just need to run sendmail in debug mode "-dx.x" where x.x is the level of logging. There's many types, and depending on the version of sendmail you're using. I cannot go into the details there. All the logs will be by default directed to syslogs file. There you go with all the messages & mail header. Becareful when you run this on a large gateway, it will use excessive space and CPU. And could cause the mail server to crawl.
   To make the answer short, install a mail gateway. The default logging will log all sender/address. Should be sufficient in your case.

Author Comment

ID: 1587821
Thank you very much.. You have been most helpfull.....


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