Re: outgoing email monitoring

http://www.securecomputing.com/index.cfm?skey=1636

http://ironport.com/products/ironport_compliance_solutions.html

Check these out, if you are looking for a gateway level complaince monitoring and e-mail policy enforcement.

They come with pre-defined compliance filters to look for things like SSN, drivers license, Credit card numbers etc...
and you can also define your own filters using regular expressions.

I have had good sucess with these products and i am sure there are many other products that can do it as well.

-Venkata Achanta