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Analyzing SMTP attachments with WireShark

Posted on 2010-09-21
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Last Modified: 2012-06-27
I use Wireshark to capture network traffic.  I can use Wireshark to view files transferred over http and I can even follow the stream of an SMTP comunication from one server to another.  I have found a way to manually copy and decode a file attachment sent with an smtp email.  

My question is, is there a way to do this automatically, given a capture file or live?  My company is suspicious of corporate espionage and we believe someone is sending emails with confidential information.
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Question by:tspeicher
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bjove earned 250 total points
ID: 33728722
You can try xplico:
http://www.xplico.org/
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Author Comment

by:tspeicher
ID: 33728890
Looks like a nice package, but it only runs on Ubuntu?  
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by:tspeicher
ID: 33728906
Sorry didn't look hard enough?
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Expert Comment

by:JoeBologna
ID: 33780418
Are you interested in statistics like the number of messages and end points of those messages? You can track destinations of messages and dashboard to get a view. Software that tackles this problem tends to cost $$$. Not sure what your budget is.
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Author Comment

by:tspeicher
ID: 33785267
I am looking to reassemble emails from the wireshark capture file.  I can do it manually, including grabbing the attachments and decoding them and naming them with the original name.  But I want something that will decode all of the emails contained in a capture file.
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Author Comment

by:tspeicher
ID: 33834017
I was looking for a Windows based solution.  But I guess I'm out of luck.
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Assisted Solution

by:JoeBologna
JoeBologna earned 250 total points
ID: 33854695
You can try ApplicationVantage by Compuware. This will take the capture file and give you a thread level view for each email communication. Is it all clear text over the wire? The one down side is that this is turn on/off technology with no monitoring capability. It's a transaction profiling tool. I used this tool to traige many customers in the past and it saves the day when problems are on the plate.
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Author Comment

by:tspeicher
ID: 33963964
Thanks for your info.
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