Restrict sending of email to certain email addresses and restrict use of attachments in Outlook

I have a client that needs to restrict who their users send emails to and also restrict their ability to send attachments in MS Outlook.  I have found solutions that work with MS Exchange to accomplish this, however, MS Exchange is not an option in this setting.  The optimum solution would be a software add-in that will create some sort of white list that the users can send to and restrict them from sending attachments either at all -OR- to only those in their white list.  The solution should also be one that is not easily circumvented by the user as the client needs to prevent the sharing of proprietary designs with competetion.  The client can migrate to another email client other than Outlook if there is one that can accomplish this.
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You're hearing about Exchange a lot, because that's simply the way it's primarily done in 2006. If Exchange is not an option, how are the users currently accessing company email, if any? If there is no centralized email, is the concern that users might email through free email sites such as gmail or hotmail? It depends on your current setup. If there is no central server, then your options range from locally installed "parental control" software solutions or more robust and much more expensive content control hardware/software solutions such as:

There are also some options available via local group policy or server, if users are accessing the network that way.

Let me know how you currently connect from that location and how many users need to be restricted. That will give us a better idea of your needs. Thanks.
nirvanawhiteAuthor Commented:
Currently the users in this small group do not have email at all.  I've got them locked down from accessing webmail or any other website outside of the company website.  There are 3 users on the design team that need to be restricted to sending emails to only certain individuals.  There is no central server as the client does not wish these 3 to be on the corporate domain that is supported by their in-house IT.  The machines are on a completely separate DSL network than the rest of the corporate machines.  I've looked at several parental control packages and haven't found one that gives us the level of control over email that we need.  I looked over the entrust solution you posted and I believe that is overkill for this situation as there is no central server.  Thanks in advance for your help.
I see. You have three people kinda floating outside of the core group that you want to keep isolated. Most of this functionality is almost always server-based; Windows Digital Rights Management comes to mind for example; it's built into Outlook 2003, but requires a server to function. Some other names that pop into my mind might help ya out:

Workshare is a Microsoft-only shop that might work for ya:

PortAuthority has been around for years in this area:

SurfControl makes a range a products from those parental control packages to enterprise-strength solutions:

See if any of these are hits for ya. If not, let me know.

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nirvanawhiteAuthor Commented:
Thank you for the links.  I'll be downloading the trial for WorkShare Protect to see if it will meet the requirements - the information on the website is a bit sketchy as to it's exact capabilities.  The portauthority product looks like another excellent product that I will keep in mind for other clients with much larger requirement and more financial backing - the $25,000 starting price tag is very steep for a solution to govern 3 employees.  Lastly, the surfcontrol appears to be another excellent program that I will definitely keep in mind for other clients, but it requires a server through which smtp is piped to run and since there is no server this will not work in this case.  I'll post my findings with WorkShare Protect after I've had the ability to download and test the solution.  Thank You for the information and the prompt followups!
This site is an example of the classic theme: give and ye shall receive.

Many thanks.
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