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I want to set up email monitoring on my server. CentOS 5, qmail, kloxo (on the odd chance someone knows a feature in there I don't know about)

A specified user needs to be able to see all incoming/outgoing mail from specific email accounts on their domain. This should be invisible to the users of those accounts. I already have something working for incoming messages (simple forwarding), so the biggest concern is getting a copy of the outbound messages.

I am open to solutions that will allow me to better manage the inbound stuff too - I like to make things easy on people. Being able to easily turn on/off accounts as well as send it all to a specific mail account would be ideal. Free software solutions are fine, but I don't mind getting my hands dirty to make this work (sometimes I prefer it)

Note: We're aware of the legalities - a written policy allowing this is already in place.

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A written policy might not be enough, depending on the system and relationship you have with users you monitor. In many places this is considered wiretapping, and you can end up in jail. I would strongly suggest you speak to a lawyer before doing this kind of stuff. –  pehrs Nov 8 '10 at 19:26
    
The legal stuff is taken care of. I agree it's important and worth mentioning for other people reading this. –  Syntax Error Nov 8 '10 at 20:00
    
@pehrs, while IANAL, if the policy indicates the system belongs to $WORK, then all contents do, too: I have never seen an employer that couldn't look through corporate email any time they wanted to without fear of reprisal since it's "their" data anyways –  warren Nov 17 '10 at 2:39
    
@warren It depends on the country. In some European countries an employer is not allowed to read personal messages sent to an employee, even if they are sent over a server belonging to $WORK, just like they are not allowed to read personal snail-mail sent to your work place. To get some idea of the issues with wiretap laws in America you can start with reading articles.techrepublic.com.com/5100-22_11-5615878.html and rcfp.org/taping/quick.html –  pehrs Nov 17 '10 at 16:27

2 Answers 2

Hey, tell you a freeware to monitor emails - capsa - http://www.colasoft.com/capsa/features.php

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This looks like it might be ideal. For anyone reading this - it looks like a client side program that does indeed have the option to monitor all emails sent/recd on the network and save the actual emails to a folder. This link mentions that feature colasoft.com/capsa/… –  Syntax Error Nov 10 '10 at 15:32
    
Have you installed this before and is it tricky? I would have to help non-technical people install this over the phone - they're far away from me. I'm slightly apprehensive about that. –  Syntax Error Nov 10 '10 at 15:57
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this kind of tool requires SPAN on the switch. you need to know the switch. –  MichaelB51026 Nov 11 '10 at 8:32

There are Nagios plugins that will do much of what you are describing. They are easily extended. http://exchange.nagios.org/directory/Plugins/Email-and-Groupware

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I'm sorry but I looked through those plugins and I see nothing helpful. Looks like a bunch of plugins for other functionality like sending test emails and checking against blacklists. –  Syntax Error Nov 17 '10 at 4:38

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