There are alot of thibgs you can do before gettibg invasive on the PC.  
Software on the PC will likely set off alarms with AV.  I'd focus more on 
native audit logging capabilities of the systems and data you want to be 
monitoring.

I'd suggest:

1. Take a forensic image of the workstation (this is a point in time snapshot 
and may provide insight into what he has been doing in the past).  Internet 
history may be useful if you do not have a proxy server that logs access.  It 
may also provide an indication if he has copied data to the PC.

2. Ensure NTFS permissions are set appropriately on sensitive resources 
(applications, folders, etc).  Enable file level auditing to determine if he 
accesses those files.

3.  Enable additional logging on the PC.  You may be able to log what 
applications are being launched and if data is being copied to the PC.

4. Review outbound email for the user at the server.  Get a copy of their 
mailbox to review.

5. Get a copy of their home directory.

6. PBX records to get a log of inbound and outbound calls.

7.  Review his access to confirm what he does and doesn't have access to. (This 
can help frame the potential scope of exposure if you assume the worst).

Sent from my iPhone

On May 25, 2013, at 11:26 PM, Dan Baxter <[email protected]> wrote:

> Okay, yesterday at work, I was asked if I could deploy some spyware to a PC 
> to determine what a particular user is doing.  The requestor was one of our 
> corporate attorneys, no less.  
> 
> The concern is that this individual is possibly accessing sensitive documents 
> and getting them to a competitor.  I'm not at this location, so I don't know 
> the person, or the exact circumstances or requirements, yet.  I have been 
> told he's the "unofficial IT guy" for this location, so he may be wary.  
> 
> At present, we don't block access to USB drives.  We do block access to cloud 
> based storage (Dropbox, Copy, Skydrive, etc).  
> 
> Ironically, this is the same atty that helped shoot down a DLP project I was 
> working on earlier this year.  I took gratification in pissing her off by 
> reminding her that this would be a perfect example of why we need one.  
> 
> Anyway, assuming I get signoff from HR and our Ethics department (still 
> questionable), are there any suggestions of what I could deploy?  Also, I 
> realize some testing is going to need to be done to make sure it doesn't set 
> off alarms on his A/V.  Any other pitfalls I need to be aware of?  
> 
> Thanks in advance.
> 
> 
> Dan Baxter
> -------------------------------------------------
> Quis custodiet ipsos custodes?
> 
> "A sword never kills anybody; it is a tool in the killers hands."-Lucius 
> Annaeus Seneca, c.4BC-65AD
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