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monitor smtp traffic

Posted on 2009-05-14
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Last Modified: 2012-05-07
I would like to montor an SMTP traffice going between 2 computers.
I don't have an email server(Exchange server, Domino,etc...).
I wonder if it's enough just to install SMTP service in both computers and download a tool(if there is any) from internet and test SMTP connection.

Thanks
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Question by:jskfan
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by:Sjef Bosman
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To monitor SMTP traffic, you can install WireShark on a third system.

You can set up a simple email server, e.g. using Linux, or any free SMTP server you can find. This one is freeware, seems a pretty popular one:
http://www.tucows.com/preview/195629
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by:jskfan
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I am using 2 windows 2003 server boxes.
How do I start your approach?
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by:Sjef Bosman
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Download and install the server software, create some accounts and start outlook to send mail from one of the accounts to another one.
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by:jskfan
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I installed the sambar server 7.0, where do I add users.
any more step by step to get it working, please?
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by:Sjef Bosman
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Apparently, Sambar only has an SMTP proxy and is not a complete server. Anyway, I couldn't find it either how to create users. So sorry...

Maybe this server is better, it seems to be anyway:
http://www.tucows.com/preview/601968
"MDaemon FREE mail server software is a 5-user license version of the award-winning MDaemon Email Server for Windows."
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by:jskfan
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I have enabled SMTP service in one computer and Telneted to it from another computer on port 25.
example: Telnet  10.10.10.10 25

would that be enough to test SMTP connection between 2 computers?
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by:Sjef Bosman
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Enough? No. You've only established that there's a server on the other side but you don't have proof that it works 100% correctly. The least you can do is create some SMTP-users on the server and use Outlook to those users. E.G. set up John Doe and Jack Chit on the server. Create an Outlook account for John Doe, and send some mails to the server for Jack Chit. Check on the server that mail arrived (there must be logs). Now you've tested SMTP communication.

If you want to test POP3 communication as well, set up an Outlook account for Jack Chit (on the same or on a different system), and try to receive your mail.
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by:Ghousullah
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Please confirm why you need to test SMTP traffic. Based on your requirement I can suggest you the options.
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by:jskfan
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I don't have an SMTP server such as Exchange server. I have enabled SMTP services in one computer(SMTPCOMPUTER), then trying to telnet to it through port 25.
for test purposes,There are some computer to which I permitted TCP 25 Through IPSec policy, and they can telnet on port 25 to SMTPCOMPUTER, but the other ones to which I Required Security, it shows Negotiate Security when I telenet on port 25 to SMTPCOMPUTER.

Now my question is the SMTP Traffic flowing between the computers to which I REquired Security on port 25 to the SMTPCOMPUTER or the SMTP traffic is blocked. How do I know that?
Unfortunately we don't manage our exchange server, unless if I can get some help to how to relay and email to the exchange server using the SMTPCOMPUTER.
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by:jskfan
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Ghousullah:

I want SMTP traffic between 2 computers to be secure.
I want to confirm that it's flowing between 2 computers in a secure way.
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by:Sjef Bosman
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Then don't use port 25, instead use port 465 and Secure SMTP with SSL.

Did you already download WireShark?? http://www.wireshark.org/
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by:jskfan
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<<Then don't use port 25, instead use port 465 and Secure SMTP with SSL.>>

I am using IPSec inside the LAN so it's Active Directory Kerberos ,not Certificate.
when teleneting to port 25 , you are testing SMTP I believe. that's what I am doing.
I downloaded wireshark. I also use Network Monitor to capture traffic between 2 computers it shows ESP frames, that means secure. Correct?

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by:jskfan
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any updates?
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Sjef Bosman earned 500 total points
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I have no detailed knowledge of IP or TCP/IP, so I can't tell if it's secure. Maybe this question should be added to the TCPIP Topic Area of EE?
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