I guess that depends of how they "encrypt" it - some schemes can be as simple as an XOR or other trivial obfuscation.  Other issues can be just related to file format of an upload / download that makes it hard to decipher the payload from a raw pcap file.   
  
Are there any tools available to simplify this process? 
  
Thanks, 
JB 
  
Ps. We are covered legally on this.  
  --- On Thu, 9/25/08, Jaap Keuter <jaap.keuter@xxxxxxxxx> wrote:
  
From: Jaap Keuter <jaap.keuter@xxxxxxxxx> Subject: Re: [Wireshark-users] Decrypted session transcripts from pcap? To: jimbalo22@xxxxxxxxx, "Community support list for Wireshark" <wireshark-users@xxxxxxxxxxxxx> Date: Thursday, September 25, 2008, 10:59 PM
 
 Hi Jim,
Well, without proper keys that is going to be a problem.
And also: make sure you've got the legal angle covered! These are tricky
subjects.
Thanx,
Jaap
Jim Balo wrote:
> The other day we had a situation where an employee was involved in some 
> questionable activities.  We were concerned that sensitive data had left 
> the company, so I analyzed the pcaps from this employees Internet 
> activities.  I found some suspcious MSN messenger sessions (over regular 
> port 80), but the payload appeared to be encrypted, making it a real 
> pain to try find out what actually took place. 
>  
> Is there any tool out there that can generate decrypted (or similar) 
> session transcripts from pcap files for common protocols (like messenger)?
>  
> Some sessions involve ftp uploads, and since I have the full pcap files, 
> I should be able to recreate the file uploaded so that I can view it in 
> the proper app (like a word or excel file) - is there any tool for this 
> out there?
>  
> Thanks,
> JB
> 
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